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2-Bromo-1,1-dimethoxyethane → HCID 178461078, compound

HRID 242081
Notes
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Reaction equation

HRID 242081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]3/[C:32](/[NH:44]C(=O)OCC3C=CC=CC=3)=[N:33]/C(=O)OCC3C=CC=CC=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH2:59][CH:60]([O:63][CH3:64])[O:61][CH3:62]>C(O)C>[CH3:62][O:61][CH:60]([O:63][CH3:64])[CH2:59][NH:44][C:32]([N:13]1[CH2:14][CH2:15][C:16]2[C:21](=[CH:20][C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])=[CH:18][CH:17]=2)[CH:12]1[C:8]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:11][CH2:10][CH2:9]1)=[NH:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 10942334Sodium MethoxideHCID 88239773benzyl (NE)-N-[[1-[1-(4-fluorophenyl)cyclobutyl]-7-[2-(propylsulfonylamino)ethoxy]-3,4-dihydro-1H-isoquinolin-2-yl]-(phenylmethoxycarbonylamino)methylidene]carbamate

Product 1

HCID 178461078HCID 178461078, compound

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
120 °C

Procedure

1-[1-(4-Fluorophenyl)cyclobutyl]-7-{2-[(propylsulfonyl)amino]ethoxy}-3,4-dihydroisoquinoline-2(1H)-carboximidamide acetate (140 mg, 0.255 mmol, cf. example 72) was suspended in ethanol (2 mL). Sodium methylate (138 mg, 0.142 mmol) and 2-bromo-1,1-dimethoxyethane (65 mg, 0.383 mmol) were added. The reaction mixture was stirred at 120° C. in the microwave (80 W) for 80 min. The solvent was evaporated in vacuo and the crude product was used without further purification for the next step.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude product was used without further purification for the next step

Sources & evidence

ORD record
ord-4cac079217a84d5ab6d38e3476be0c93
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653100B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes