Triethylamine → HCID 23537499, compound

HRID 1792496Notes

Reaction equation

HRID 1792496 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[C:14]([F:21])[CH:13]=1.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:25][CH:22]2[CH2:24][CH2:23]2)=[O:17])=[C:14]([F:21])[CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22031248HCID 22031248, compound

Product 1

HCID 23537499HCID 23537499, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.2 g 4-(6-chloroquinazolin-4-yl)-2-fluorobenzoic acid (compound in Production Example 386), 41 mg cyclopropylamine and 0.12 mL triethylamine were dissolved in 6 mL dichloromethane, then 320 mg benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate was added thereto, and the mixture was stirred at room temperature for 3 hours. The reaction solution was purified by NH silica gel column chromatography (hexane/ethyl acetate) and then recrystallized from methanol/ethyl acetate/ether, to give 162 mg of the title compound as colorless crystals.

Workup

  1. customThe reaction solution was purified by NH silica gel column chromatography (hexane/ethyl acetate)
  2. customrecrystallized from methanol/ethyl acetate/ether

Sources & evidence

ORD record
ord-6166f5ee7a5447d7a41b08353050cb49
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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