Hydrochloric Acid → HCID 21109109, compound

HRID 1766093Notes

Reaction equation

HRID 1766093 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:27])[CH2:25]Br)[CH:18]=3)=[N:10][C:11]([S:15][CH3:16])=[N:12]2)=[C:7]([NH2:28])[C:6]=1[C:29]([NH2:31])=[O:30])([CH3:4])([CH3:3])[CH3:2].[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.O.Cl>C(#N)C.C(Cl)Cl>[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:27])[CH2:25][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:18]=3)=[N:10][C:11]([S:15][CH3:16])=[N:12]2)=[C:7]([NH2:28])[C:6]=1[C:29]([NH2:31])=[O:30])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8083MorpholineHCID 21109108HCID 21109108, compound

Product 1

HCID 21109109HCID 21109109, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-amino-2-methylthio-4-(3-(2-bromoacetamido)-phenyl)-quinazoline-6-carboxamide (example 28a, 88 mg) in acetonitrile was added morpholine (148 l) and the mixture was stirred for 18 h. After this time CH2Cl2 (15 ml) was added and the mixture was washed with sat. aqueous NaHCO3. The organic layer was dried (MgSO4) and concentrated in vacuo. The title compound was purified by chromatography on silica gel using CH2Cl2MeOH=1/0 to 9/1 (v/v) as eluent. The title compound was lyophilized from a mixture of acetonitrile and water containing 1.5 equiv. of HCl.

Workup

  1. washthe mixture was washed with sat. aqueous NaHCO3
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe title compound was purified by chromatography on silica gel using CH2Cl2MeOH=1/0 to 9/1 (v/v) as eluent

Sources & evidence

ORD record
ord-b2e9808819b24da0ab99df07915de5a2
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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