1-(1h-Indol-5-yl)ethylamine adipate → N2-((4-chloro-1H-indol-5-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methylpyrimidine-2,4-diamine

HRID 475246Notes

Reaction equation

HRID 475246 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([Cl:19])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C(OC(C)(C)C)=O)[CH:7]=[CH:6]2.Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[CH:32]=[C:31]([CH:33]3[CH2:35][CH2:34]3)[NH:30][N:29]=2)[CH:24]=[CH:23][N:22]=1.[C:36](O)(=O)CCCCC(O)=O.N1C2C(=CC(C(N)C)=CC=2)C=C1>>[Cl:19][C:4]1[C:3]([CH2:2][NH:1][C:21]2[N:26]=[C:25]([NH:27][C:28]3[CH:32]=[C:31]([CH:33]4[CH2:35][CH2:34]4)[NH:30][N:29]=3)[CH:24]=[C:23]([CH3:36])[N:22]=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

4

Reactant 3

HCID 529934411-(1h-Indol-5-yl)ethylamine adipateHCID 581691182-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 71272344tert-butyl 5-(aminomethyl)-4-chloro-1H-indole-1-carboxylate

Product 1

HCID 86694737N2-((4-chloro-1H-indol-5-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methylpyrimidine-2,4-diamine

Procedure

N2-((4-chloro-1H-indol-5-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methylpyrimidine-2,4-diamine (I-19) was prepared in accord with the procedure in example 19 except in step 1, 185 and tert-butyl 5-(aminomethyl)-4-chloro-1H-indole-1-carboxylate were used in place of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine and 1-(1H-indol-5-yl)ethanamine adipic acid salt to afford I-19.

Workup

  1. customto afford I-19

Sources & evidence

ORD record
ord-b507a3023e7049beab9cb97b26ce6136
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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