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 475305Notes

Reaction equation

HRID 475305 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[C:4]([CH3:17])[N:3]=1.[NH2:18][CH2:19][C:20]1[C:21]([Cl:36])=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25](C(OC(C)(C)C)=O)[CH:24]=[CH:23]2.ClC1N=C(NC2NN=C(C3CC3)C=2)C=CN=1.C(O)(=O)CCCCC(O)=O.N1C2C(=CC(C(N)C)=CC=2)C=C1>>[Cl:36][C:21]1[C:20]([CH2:19][NH:18][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([CH:14]4[CH2:16][CH2:15]4)[NH:11][N:10]=3)[CH:5]=[C:4]([CH3:17])[N:3]=2)=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[CH:24][NH:25]2

Participants

5

Reactant 4

HCID 529934411-(1h-Indol-5-yl)ethylamine adipateHCID 598196152-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-6-methylpyrimidin-4-amineHCID 71272344tert-butyl 5-(aminomethyl)-4-chloro-1H-indole-1-carboxylateHCID 178478345HCID 178478345, compound

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 using procedure analogous to the preparation of I-8, step 1, except 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methyl-pyrimidin-4-amine 185 and tert-butyl 5-(aminomethyl)-4-chloro-1H-indole-1-carboxylate were used in place of 53 and 1-(1H-indol-5-yl)ethanamine adipic acid salt, respectively, to afford I-19; MS (ESI) m/z=394.1 [M+1]+.

Workup

  1. customanalogous to the preparation of I-8, step 1
  2. customrespectively, to afford I-19

Sources & evidence

ORD record
ord-643f4f5e95d94045b3eaad172b52906f
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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