Thiomorpholine → HCID 69288632, compound

HRID 1766104Notes

Reaction equation

HRID 1766104 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[C:7]([NH:11][C:12]([C:14]1[S:47][C:17]2[N:18]=[C:19]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29](OC4C=CC([N+]([O-])=O)=CC=4)=[O:30])[CH:23]=3)[C:16]=2[C:15]=1[NH2:48])=[O:13])([CH3:10])([CH3:9])[CH3:8]>ClCCl>[C:7]([NH:11][C:12]([C:14]1[S:47][C:17]2[N:18]=[C:19]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]([N:1]4[CH2:6][CH2:5][S:4][CH2:3][CH2:2]4)=[O:30])[CH:23]=3)[C:16]=2[C:15]=1[NH2:48])=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 69037811HCID 69037811, compound

Product 1

HCID 69288632HCID 69288632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thiomorpholine (300 μl) was added to a solution of tert-butyl 5-amino-2-phenyl-4-(3-(p-nitro-phenoxycarbonylamino)-phenyl)-thieno[2,3-d]pyrimidine-6-carboxamide (example 31(h), 150 mg) in dichloromethane (5 ml) and the reaction mixture was stirred at room temperature overnight. Subsequently, the reaction mixture was diluted with CH2Cl2 and washed with H2O. The organic layer was concentrated under reduced pressure. The title compound was purified by HPLC using a Luna C-18 column with the following gradient: H2O/CH3CN=80/20 to 0/100 (v/v) in 45 min. The title compound was then lyophilized from a mixture of 1,4-dioxane and H2O.

Workup

  1. washwashed with H2O
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe title compound was purified by HPLC
  4. waitH2O/CH3CN=80/20 to 0/100 (v/v) in 45 min
  5. additionThe title compound was then lyophilized from a mixture of 1,4-dioxane and H2O

Sources & evidence

ORD record
ord-a52827afe3124fc4b18f71b4ecd36524
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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