4-(Aminomethyl)-2-chlorophenol hydrobromide → HCID 58603374, compound

HRID 2386515Notes

Reaction equation

HRID 2386515 reaction equation
C(OC(=O)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH:13]=1)[CH:8]([CH3:10])[CH3:9])(C)(C)C.Br.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([Cl:36])[CH:30]=1>>[Cl:36][C:31]1[CH:30]=[C:29]([CH2:28][NH:27][C:20]2[N:19]=[C:18]([C:14]3[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][NH:7][CH:8]([CH3:9])[CH3:10])[CH:13]=3)[CH:23]=[CH:22][N:21]=2)[CH:34]=[CH:33][C:32]=1[OH:35]

Participants

3

Reactant 2

HCID 670455344-(Aminomethyl)-2-chlorophenol hydrobromide2×HCID 86603285[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-isopropyl-carbamic acid tert-butyl ester2×

Product 1

HCID 58603374HCID 58603374, compound

Procedure

[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-isopropyl-carbamic acid tert-butyl ester (intermediate 70) was coupled with 4-Aminomethyl-2-chloro-phenol hydrobromide salt (Intermediate 121) following procedure F then deprotected by procedure G. LC-MS showed the product had the expected M+H+ of 383. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.31 ppm) δ 8.5 (s, 1H) 8.4 (d, 1H) 8.3 (d, 1H) 7.8 (d, 1H) 7.7 (m, 1H) 7.6 (d, 1H) 7.4 (s, 1H) 7.2 (d, 1H) 6.9 (d, 1H) 4.3 (s, 1H) 3.6 (m, 2H) 3.5 (m, 1H) 1.4 (d, 6H)

Sources & evidence

ORD record
ord-7f7b354ddb974c7abe2c99fdb8afd385
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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