Triethylamine → HCID 21192738, compound

HRID 1418397Notes

Reaction equation

HRID 1418397 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH2:15])=[N:5][C:6]1([CH2:14][NH:13][CH2:12]1)[NH:7]2.C(N(CC)CC)C.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](Cl)=[O:29]>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH2:15])=[N:5][C:6]1([CH2:12][N:13]([C:28]([C:24]3[S:23][CH:27]=[CH:26][CH:25]=3)=[O:29])[CH2:14]1)[NH:7]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 21192802HCID 21192802, compound

Product 1

HCID 21192738HCID 21192738, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5'-Fluorospiro[azetidine-3,2'(1'H)quinazoline]-4'-amine (Example 250, 206 mg, 1 mmol) and triethylamine (0.28 ml., 2 mmol) in dry dichloromethane (15 ml) was stirred at 20° C. and thiophene-2-carbonyl chloride (0.12 ml, 1.1 mmol) added. The mixture was stirred at ambient temperature for 3 h then concentrated to dryness and separated by flash chromatography on silica using dichloromethane/methanol mixtures as eluant. The more polar fraction eluted afforded the title compound (50 mg) as a solid, m.p. 214°-215° C.

Workup

  1. concentrationthen concentrated to dryness
  2. customseparated by flash chromatography on silica
  3. washThe more polar fraction eluted

Sources & evidence

ORD record
ord-7a7193ff7c7143adae047f35368595e8
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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