1-Cycloheptenylboronic acid pinacol ester → (R,E)-5-Amino-N-(5-(4-aminoazepan-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-cycloheptenylthiazole-4-carboxamide

HRID 2089435Notes

Reaction equation

HRID 2089435 reaction equation
Br[C:2]1[S:3][C:4]([NH:30]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:29])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:28])[C:13]=2[N:14]2[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21]C(=O)C(F)(F)F)[CH2:16][CH2:15]2)[N:6]=1.[C:38]1(B2OC(C)(C)C(C)(C)O2)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH:39]=1>>[NH2:30][C:4]1[S:3][C:2]([C:38]2=[CH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]2)=[N:6][C:5]=1[C:7]([NH:8][C:9]1[CH:10]=[N:11][N:12]([CH3:28])[C:13]=1[N:14]1[CH2:20][CH2:19][CH2:18][C@@H:17]([NH2:21])[CH2:16][CH2:15]1)=[O:29]

Participants

3

Reactant 2

HCID 154866091-Cycloheptenylboronic acid pinacol esterHCID 86658426(R)-tert-butyl 2-bromo-4-(1-methyl-5-(4-(2,2,2-trifluoroacetamido)-azepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate

Product 1

HCID 58465012(R,E)-5-Amino-N-(5-(4-aminoazepan-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-cycloheptenylthiazole-4-carboxamideYield 14%

Procedure

Following the procedure for Example 350 starting with (R)-tert-butyl 2-bromo-4-(1-methyl-5-(4-(2,2,2-trifluoroacetamido)-azepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate and 1-cycloheptenylboronic acid pinacol ester gave 339 as an orange solid (7.0 mg, 14%). 1H NMR (400 MHz, d4-MeOD) δ 7.57 (s, 1H), 6.46 (t, J=6.7 Hz, 1H), 3.74 (s, 3H), 3.31-3.22 (m, 4H), 3.14-3.06 (m, 1H), 2.88-2.82 (m, 2H), 2.39-2.32 (m, 2H), 2.05-1.56 (m, 12H). LCMS (ES+) m/z 430 (M+1)

Sources & evidence

ORD record
ord-1f111a2a42354b7091b754d4f86b11cd
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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