4-Methylmorpholine → HCID 10158801, compound

HRID 1068972Notes

Reaction equation

HRID 1068972 reaction equation
[Cl:1]C(OCC(C)C)=O.CN1CCOCC1.[Br:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([NH2:34])[CH:32]=3)[N:27]=[CH:26][N:25]=2)[CH:20]=[CH:21][CH:22]=1.[O:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>N1C=CC=CC=1>[Br:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([NH:34][C:36](=[O:35])[C:37]#[C:38][CH2:39][Cl:1])[CH:32]=3)[N:27]=[CH:26][N:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 10158801HCID 10158801, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Isobutyl chloroformate (0.625 g, 4.58 mmol) and N-methylmorpholine (0.506 g, 5.00 mmol) were added to an ice cold solution of 0.542 g (4.58 mmol) of 4-chloro-but-2-yanoic acid in 7mL of tetrahydrofuran under nitrogen. After stirring for 30min, a solution of 0.72 g (2.287 mmol) of N-(3-bromophenyl)-4,6-quinazolindiamine in 3.35 mL of pyridine was added and the mixture was stirred at 0° C. for 1 h. The reaction was quenched with ice water. The product was collected by filtration, washed with water and ether, and dried in vacuo to give 0.537 g of brown solid; ESMS m/z 417.0 (M+H+).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 h
  2. customThe reaction was quenched with ice water
  3. filtrationThe product was collected by filtration
  4. washwashed with water and ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ebf0bb76ff6a40388d2178eb27e41e8a
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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