Hydrochloric Acid → Hydrochloric Acid

HRID 1518305Notes

Reaction equation

HRID 1518305 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:35][CH2:36][CH2:37][OH:38])=[C:26]([C:28]([O:30]C(C)(C)C)=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[ClH:47].CO>C(Cl)Cl.CCOCC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:35][CH2:36][CH2:37][OH:38])=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[ClH:47]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59447663tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 594474832-(8-(Benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate (38E) (68 mg, 0.1 mmol) in DCM (2 mL) was added 2 mL of 2N HCl in ether. The mixture was stirred at rt overnight. MeOH (0.5 mL) was added to the mixture to dissolve the solid. The mixture was stirred at rt for another 2 hours. The reaction mixture was concentrated under reduced pressure to provide the desired product as an HCl salt: 1H NMR (300 MHz, DMSO-D6) δ ppm 8.03 (1H, d), 7.79 (1H, d), 7.67 (1H, d), 7.41 (5H, m), 4.83 (2H, s), 3.73 (4H, t), 3.50 (2H, t), 3.41 (2H, t), 3.04 (4H, t), 1.69 (2H, m). MS (ESI(+)): m/z 495 (M+H).

Workup

  1. dissolutionto dissolve the solid
  2. stirringThe mixture was stirred at rt for another 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7880a9b81d3e495999536b83d0fe826d
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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