Benzoic acid, 4-isocyano-, methyl ester (9CI) → HCID 89501782, compound

HRID 1054141Notes

Reaction equation

HRID 1054141 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:36]2[CH:40]=[N:39][N:38]=[N:37]2)=[C:6](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH3:22])[CH:18]=3)[CH:13]2[C:23]([NH:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][CH:27]=2)=[O:24])=[O:11])[CH:7]=1.[N+](C1C=CC(C(OC)=O)=CC=1)#[C-]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:36]2[CH:40]=[N:39][N:38]=[N:37]2)=[C:6](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH3:22])[CH:18]=3)[CH:13]2[C:23]([NH:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)=[O:24])=[O:11])[CH:7]=1

Participants

4

Reactant 2

HCID 2759891Benzoic acid, 4-isocyano-, methyl ester (9CI)HCID 131733304HCID 131733304, compound

Product 1

HCID 89501782HCID 89501782, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-Methyl 4-(2-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acryloyl)-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamido)benzoate: To 20B (0.15 g, 1.033 mmol), methyl 4-isocyanobenzoate (0.166 g, 1.033 mmol), and Intermediate 2 (0.259 g, 1.033 mmol) was added MeOH (20 mL). The reaction was heated to reflux for 24 h. After cooling to rt the product was filtered off as (0.318 g, 55.3%) a yellow solid. MS (ESI) m/z: 557.0 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 24 h
  3. filtrationwas filtered off as (0.318 g, 55.3%) a yellow solid

Sources & evidence

ORD record
ord-b63e9da199594fcb9564eae3caf706f5
Source dataset
uspto-grants-2016_07
Patent number
US09394276B2

Reaction notes

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