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

HRID 1518293
Notes
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Reaction equation

HRID 1518293 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]([C:33]3[CH:38]=[CH:37][C:36]([CH2:39][OH:40])=[CH:35][CH:34]=3)=[C:26]([C:28]([O:30]CC)=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].Cl>O1CCOCC1.CO>[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]([C:33]3[CH:34]=[CH:35][C:36]([CH2:39][OH:40])=[CH:37][CH:38]=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59447480ethyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylate

Product 1

HCID 468370542-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887Methanol
Solvent
HCID 312751,4-DioxaneSolvent2×

Procedure

To compound 34D (0.14 g) in 1,4-dioxane (2 mL) was added 4 N HCl in 1,4-dioxane (2 mL) and MeOH (0.5 mL). The solution was stirred for 1 hour at rt, concentrated under reduced pressure, and added 1.0 N LiOH (2 mL) in 1,4-dioxane (2 mL). The solution was stirred at 60° C. for 1 hour, concentrated under reduced pressure and purified by Prep HPLC to provide the desired product 34: 1H NMR (DMSO-d6): δ 8.02 (d, J=7.98 Hz, 1H), 7.79 (d, J=7.98 Hz, 1H), 7.69 (d, J=7.36 Hz, 1H), 7.29-7.49 (m, 8H), 4.90 (s, 2H), 4.50 (s, 2H), 3.78 (t, J=5.98 Hz, 2H), 3.98 (t, J=5.98 Hz, 2H); MS (ESI(+)): m/z 543 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionadded 1.0 N LiOH (2 mL) in 1,4-dioxane (2 mL)
  3. stirringThe solution was stirred at 60° C. for 1 hour
  4. concentrationconcentrated under reduced pressure
  5. custompurified by Prep HPLC

Sources & evidence

ORD record
ord-0286c758ad3045ac8394aca811c7ed59
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232273B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes