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Water → N-(1-(hydroxymethyl)cyclopropyl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246683
Notes
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Reaction equation

HRID 246683 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[N:12]=[C:13]4[C:19]([C:20](O)=[O:21])=[CH:18][NH:17][C:14]4=[N:15][CH:16]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[NH2:34][C:35]1([CH2:38][OH:39])[CH2:37][CH2:36]1.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[OH:39][CH2:38][C:35]1([NH:34][C:20]([C:19]2[C:13]3[C:14](=[N:15][CH:16]=[C:11]([C:6]4[C:5]5[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=5)[NH:8][N:7]=4)[N:12]=3)[NH:17][CH:18]=2)=[O:21])[CH2:37][CH2:36]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 14146220(1-Aminocyclopropyl)methanolHCID 712798942-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 71280082N-(1-(hydroxymethyl)cyclopropyl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 8.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (100 mg, 0.34 mmol), EDCI (123 mg, 0.64 mmol) and DMAP (110 mg, 0.90 mmol) in 6 mL of DMF was added (1-aminocyclopropyl)methanol (59 mg, 0.68 mmol) in one portion at room temperature, then the mixture was stirred for 16 hours. The reaction mixture was poured into 40 mL of water, filtered and the filter cake was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions were: 25% acetonitrile/75% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 50% acetonitrile/50% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give N-(1-(hydroxymethyl)cyclopropyl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (10 mg, 8.1%) as a yellow solid. MS: (M+H)+=363; 1H NMR (300 MHz, DMSO): δ 13.36 (s, 1H), 12.81 (s, 1H), 9.16 (s, 1H), 8.75 (s, 1H), 8.40-8.38 (m, 2H), 7.43 (s, 1H), 7.16 (d, 1H, J=8.7 Hz), 4.89 (brs, 1H), 3.59 (brs, 2H), 2.54 (s, 3H), 0.92-0.83 (m, 4H).

Workup

  1. filtrationfiltered
  2. customthe filter cake was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm
  3. wait25% acetonitrile/75% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 50% acetonitrile/50% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.

Sources & evidence

ORD record
ord-9e4c603539a9443d97ec7bb25e18c3e2
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658646B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes