Triethylamine → HCID 69373698, compound

HRID 1168692Notes

Reaction equation

HRID 1168692 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:39][CH2:40][CH:41]4[CH2:43][CH2:42]4)=[C:24]([NH:27][C:28](=[O:38])[CH:29]=[CH:30][CH2:31][N:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15].Br[CH:45]1[CH2:49][CH2:48][O:47][C:46]1=[O:50]>O1CCCC1>[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:39][CH2:40][CH:41]4[CH2:42][CH2:43]4)=[C:24]([NH:27][C:28](=[O:38])[CH:29]=[CH:30][CH2:31][N:32]4[CH2:37][CH2:36][N:35]([CH:45]5[CH2:49][CH2:48][O:47][C:46]5=[O:50])[CH2:34][CH2:33]4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 53675098HCID 53675098, compound

Product 1

HCID 69373698HCID 69373698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.42 ml of triethylamine is added to 608 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-{[4-(piperazin-1-yl)-1-oxo-2-buten-1-yl]amino}-7-cyclopropylmethoxyquinazoline in 3.0 ml of tetrahydrofuran. The mixture is cooled in the ice bath and a solution of 215 mg of 3-bromodihydrofuran-2-one in 1.0 ml of tetrahydrofuran is added dropwise and the mixture is stirred for one hour with cooling. The ice bath is then removed and the mixture is stirred for about 48 hours at ambient temperature. The reaction mixture is chromatographed directly, without further processing, over a silica gel column, with methylene chloride/methanol (95:5 to 90:10) as eluant. The foamy crude product is crystallized by trituration with a little diethylether.

Workup

  1. temperaturewith cooling
  2. customThe ice bath is then removed
  3. stirringthe mixture is stirred for about 48 hours at ambient temperature
  4. customThe reaction mixture is chromatographed directly, without further processing, over a silica gel column, with methylene chloride/methanol (95:5 to 90:10) as eluant
  5. customThe foamy crude product is crystallized by trituration with a little diethylether

Sources & evidence

ORD record
ord-3918353de41f4d74b71b9d86e076b7da
Source dataset
uspto-grants-2003_09
Patent number
US06627634B2

Reaction notes

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