HCID 58459119, compound → HCID 58459244, compound

HRID 2036616Notes

Reaction equation

HRID 2036616 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:15]([CH:16]3[CH2:18][CH2:17]3)[C:14]3[C:19]([C:23](OC)=[O:24])=[CH:20][CH:21]=[CH:22][C:13]=3[N:12]=2)[CH3:10])[C:3]=1[C:27]#[N:28].N[C@H](C1N(C2CC2)C2C(C([NH:46][C:47]([CH3:50])([CH3:49])[CH3:48])=O)=CC=CC=2N=1)C>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:15]([CH:16]3[CH2:18][CH2:17]3)[C:14]3[C:19]([C:23]([NH:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:24])=[CH:20][CH:21]=[CH:22][C:13]=3[N:12]=2)[CH3:10])[C:3]=1[C:27]#[N:28]

Participants

3

Reactant 2

HCID 58459119HCID 58459119, compoundHCID 58459391HCID 58459391, compound

Product 1

HCID 58459244HCID 58459244, compound

Procedure

Using the general synthetic procedure for (S)-methyl 2-(1-(6-amino-5-cyanopyrimidin-4-ylamino)ethyl)-1-cyclopropyl-1H-benzo[d]imidazole-7-carboxylate in example 47, 2-((1S)-1-((6-amino-5-cyano-4-pyrimidinyl)amino)ethyl)-N-tert-butyl-1-cyclopropyl-1H-benzimidazole-7-carboxamidewas prepared using (S)-2-(1-amino ethyl)-N-tert-butyl-1-cyclopropyl-1H-benzo[d]imidazole-7-carboxamide: 1H NMR (400 MHz, MeOH-d4) δ 8.03 (1H, s), 7.68 (1H, d, J=8.0 Hz), 7.38 (1H, d, J=8.0 Hz), 7.27 (1H, t, J=8.0 Hz), 6.04 (1H, q, J=8.0 Hz), 3.55-3.43 (1H, m), 3.03-2.96 (1H, m), 1.73 (3H, d, J=4.0 Hz), 1.53 (9H, s), 1.40-1.30 (1H, m), 1.30-1.15 (2H, m), 1.10-0.93 (1H, m); LC-MS (ESI) m/z 419.2 [M+H]+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-f460ed868e8c4d2a8d837a7ea8d2d74f
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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