Ethylmorpholine → 3-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid (1-cyclopropyl-piperidin-4-yl)-amide

HRID 2234132Notes

Reaction equation

HRID 2234132 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]([OH:18])=O)[CH:14]=3)[NH:9][C:8]=2[C:19]2[C:20](=[O:31])[NH:21][N:22]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH:24]=2)[CH:4]=[N:3]1.C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH:62]1([N:65]2[CH2:70][CH2:69][CH:68]([NH2:71])[CH2:67][CH2:66]2)[CH2:64][CH2:63]1>ClCCl>[CH:62]1([N:65]2[CH2:70][CH2:69][CH:68]([NH:71][C:16]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[NH:9][C:8]([C:19]3[C:20](=[O:31])[NH:21][N:22]=[C:23]([C:25]5[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=5)[CH:24]=3)=[C:7]4[C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[O:18])[CH2:67][CH2:66]2)[CH2:64][CH2:63]1

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 162276441-Cyclopropylpiperidin-4-amineHCID 1359618733-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid

Product 1

HCID 1359618163-(1-Methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid (1-cyclopropyl-piperidin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg of 3-(1-methyl-1H-pyrazol-4-yl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)-1H-indole-5-carboxylic acid is dissolved in 3 ml of dichloromethane and 139 mg of N-ethylmorpholine and 43.6 mg of TOTU (O-((ethoxycarbonyl)-cyanomehyleneamino)-N,N, N′,N′-tetramethyluroniumtetrafluoro) is added. After 5 minutes 34 mg of 1-cyclopropyl-piperidin-4-ylamine is added. The reaction is stirred for 48 h at RT. The product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 47 mg. LC-MS (ES+) 535 (M+H)+.

Workup

  1. customThe product is purified by preparative RP-HPLC
  2. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)

Sources & evidence

ORD record
ord-cfdb77dbdec246028056d5888c22c08b
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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