Triethylamine → HCID 71255874, compound

HRID 540213Notes

Reaction equation

HRID 540213 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2([N:18]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:17][O:16][CH2:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:33])[CH:8]=2)[N:3]=1.[S:34]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[CH2:38][NH:37][CH2:36][CH2:35]1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:18]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1([CH2:13][NH:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:33])[CH:8]=3)[N:3]=[C:2]([N:37]3[CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[S:34][CH2:35][CH2:36]3)[N:11]=2)[CH2:17][O:16][CH2:15]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepineHCID 86691408HCID 86691408, compound

Product 1

HCID 71255874HCID 71255874, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (2-chloro-6-methylquinazolin-4-yl)-[3-(dibenzylamino)oxetan-3-ylmethyl]-amine (2 g, 4.4 mmol, prepared in analogy to N-(3-aminooxetan-3-ylmethyl)-2-chloro-6-methylquinazolin-4-amine in Example 55-1), 2,3,4,5-tetrahydro-1,4-benzothiazepine (720 mg, 4.4 mmol), triethylamine (1.2 mL, 8.6 mmol) in N,N-dimethylformamide (20 mL) was heated with stirring in a 30 mL of microwave process vial for 2 hours at 150° C. The reaction mixture was diluted with ethyl acetate, washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 1.7 g of the product as a white solid.

Workup

  1. temperaturewas heated
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e35a49f4a640488cad107416f9c0f515
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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