5-(Boc-amino)-thiazole-4-carboxylic acid → (R)-5-amino-N-(5-(4-aminoazepan-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-(5-bromo-2-fluorophenyl)thiazole-4-carboxamide

HRID 2089419Notes

Reaction equation

HRID 2089419 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:25])[C:6]=1[N:7]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14]C(=O)OCC2C=CC=CC=2)[CH2:9][CH2:8]1.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([F:49])=[C:31]([C:33]2[S:34][C:35]([NH:41]C(OC(C)(C)C)=O)=[C:36]([C:38](O)=[O:39])[N:37]=2)[CH:32]=1.C(OC(NC1SC=NC=1C(O)=O)=O)(C)(C)C>>[NH2:41][C:35]1[S:34][C:33]([C:31]2[CH:32]=[C:27]([Br:26])[CH:28]=[CH:29][C:30]=2[F:49])=[N:37][C:36]=1[C:38]([NH:1][C:2]1[CH:3]=[N:4][N:5]([CH3:25])[C:6]=1[N:7]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH2:14])[CH2:9][CH2:8]1)=[O:39]

Participants

4

Reactant 3

HCID 581822035-(Boc-amino)-thiazole-4-carboxylic acidHCID 58465005(R)-benzyl 1-(4-amino-1-methyl-1H-pyrazol-5-yl)azepan-4-ylcarbamateHCID 674375972-(5-Bromo-2-fluorophenyl)-5-((tert-butoxycarbonyl)amino)thiazole-4-carboxylic acid

Product 1

HCID 58465081(R)-5-amino-N-(5-(4-aminoazepan-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-(5-bromo-2-fluorophenyl)thiazole-4-carboxamide

Procedure

Following procedures from Examples 140, (R)-benzyl 1-(4-amino-1-methyl-1H-pyrazol-5-yl)azepan-4-ylcarbamate from Example 16 and the product of Example 27, 245-bromo-2-fluorophenyl)-5-(tert-butoxycarbonylamino)thiazole-4-carboxylic acid, were converted to 308. 1H NMR (400 MHz, DMSO) δ 9.05 (s, 1H), 8.45 (dd, J=6.7, 2.5 Hz, 1H), 7.66-7.55 (m, 1H), 7.48 (s, 2H), 7.43 (s, 1H), 7.36 (dd, J=11.2, 8.9 Hz, 1H), 3.65 (s, 4H), 3.21-2.93 (m, 7H), 1.84 (dd, J=8.2, 3.6 Hz, 3H), 1.72-1.39 (m, 3H). MS (ESI) m/z: 508.1/510.1 [M+H+].

Sources & evidence

ORD record
ord-54cfbe489f3541e09fb0d15a993b5b75
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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