1-Hydroxybenzotriazole → HCID 44545044, compound

HRID 2093394Notes

Reaction equation

HRID 2093394 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][C:19]([NH2:22])=[N:20][CH:21]=3)[N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[CH2:23][CH:24]2[CH2:28][CH2:27][NH:26][CH2:25]2)[CH2:3][CH2:2]1.C1C=CC2N([OH:38])N=NC=2C=1.C(N([CH:45]([CH3:47])C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(O)(=O)C>[NH2:22][C:19]1[N:20]=[CH:21][C:16]([C:14]2[N:13]=[C:12]3[C:8]([N:9]=[CH:10][N:11]3[CH2:23][CH:24]3[CH2:28][CH2:27][N:26]([C:45](=[O:38])[CH3:47])[CH2:25]3)=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[N:15]=2)=[CH:17][N:18]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58015217HCID 58015217, compound

Product 1

HCID 44545044HCID 44545044, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

5-(6-Morpholino-9-(pyrrolidin-3-ylmethyl)-9H-purin-2-yl)pyrimidin-2-amine (75 mg) was reacted with excess acetic acid, 2 eq HOBT, 5 eq diisopropylethylamine and 2 eq N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide Hydrochloride in 1 mL of DMF. Upon completion, the reaction was extracted with ethyl acetate and a saturated sodium bicarbonate solution. The organic layer was concentrated and purified via reverse phase HPLC to give 40.1 mg 108 as a white solid. MS (Q1) 424.2 (M)+.

Workup

  1. extractionUpon completion, the reaction was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-248e040526434ae883732a027f1114e6
Source dataset
uspto-grants-2013_05
Patent number
US08445487B2

Reaction notes

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