Diisopropylethylamine → HCID 178520753, compound

HRID 1028213Notes

Reaction equation

HRID 1028213 reaction equation
[C:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:24][C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[F:34])=[O:26])[CH:20]=3)[CH2:15]2)=[O:13])[CH2:7][CH2:6]1)(O)=[O:2].[NH:35]1[C:39]([NH2:40])=[N:38][N:37]=[N:36]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>Cl.CN(C=O)C>[NH:35]1[C:39]([NH:40][C:1]([CH2:4][C@H:5]2[CH2:10][CH2:9][C@H:8]([O:11][C:12]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([NH:24][C:25]([NH:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[F:34])=[O:26])[CH:20]=4)[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)=[O:2])=[N:38][N:37]=[N:36]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178509299HCID 178509299, compoundHCID 178525569HCID 178525569, compound

Product 1

HCID 178520753HCID 178520753, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A DMF (4 mL) solution of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-carboxymethyl-cyclohexyl ester (188 mg) obtained in Example 2, 1H-tetrazol-5-ylamine (54 mg), BOP reagent (212 mg), and diisopropylethylamine (0.10 mL) was stirred overnight at room temperature. The reaction mixture was diluted with 1 N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was concentrated and vigorously stirred in water/isopropyl ether. The obtained solid was heated to reflux in methanol and collected by filtration. The title compound (99 mg, 46%) was obtained as a pale yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. temperatureThe obtained solid was heated
  4. temperatureto reflux in methanol
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d0fc415292804f20b45d618007060bf0
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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