Hydrochloric Acid → 5-(3-(4-(1H-pyrazol-4-yl)phenoxy)propyl)-2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylic acid

HRID 1518356Notes

Reaction equation

HRID 1518356 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:57]=[CH:56][C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]3[S:18][C:17]([N:19]4[CH2:28][CH2:27][C:26]5[C:21](=[C:22]([C:29](=[O:48])[N:30]([C:39]6[S:40][C:41]7[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=7[N:43]=6)COCC[Si](C)(C)C)[CH:23]=[CH:24][CH:25]=5)[CH2:20]4)=[N:16][C:15]=3[C:49]([O:51]C(C)(C)C)=[O:50])=[CH:8][CH:7]=2)[CH:3]=[N:2]1.Cl>C(Cl)Cl.CCOCC>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:57]=[CH:56][C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]3[S:18][C:17]([N:19]4[CH2:28][CH2:27][C:26]5[C:21](=[C:22]([C:29](=[O:48])[NH:30][C:39]6[S:40][C:41]7[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=7[N:43]=6)[CH:23]=[CH:24][CH:25]=5)[CH2:20]4)=[N:16][C:15]=3[C:49]([OH:51])=[O:50])=[CH:8][CH:7]=2)[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59447632tert-butyl 5-(3-(4-(1H-pyrazol-4-yl)phenoxy)propyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

Product 1

HCID 468366465-(3-(4-(1H-pyrazol-4-yl)phenoxy)propyl)-2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 73A (30 mg) in DCM (1 ml) was treated with HCl 2 N in ether (5 ml) for 2 days. The precipitate was collected and dried to give the title compound 73: 1H NMR (400 MHz, DMSO-D6) δ ppm 8.09 (2H, s), 8.02 (1H, d), 7.79 (1H, d), 7.68 (1H, d), 7.51 (2H, d), 7.44-7.48 (2H, m), 7.33-7.42 (2H, m), 6.91 (2H, d), 4.87 (2H, s), 3.99 (2H, t), 3.75 (2H, t), 3.19 (2H, t), 3.04 (2H, t); LCMS (APCI) m/e 637 (M+H).

Workup

  1. customThe precipitate was collected
  2. customdried

Sources & evidence

ORD record
ord-eb87ef8138cf487db352d7ec0a73980c
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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