Diisopropylethylamine → N-(3,4-Dichlorophenyl)-7-[(2E)-4-(1,4-oxazepan-4-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38575Notes

Reaction equation

HRID 38575 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:28][CH2:27][C:10]2[C:11]3[C:16]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=4)=[N:15][CH:14]=[N:13][C:12]=3[S:26][C:9]=2[CH2:8]1)=[O:6].CCN(C(C)C)C(C)C.Cl.[O:39]1[CH2:45][CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>CN(C=O)C>[Cl:25][C:20]1[CH:19]=[C:18]([NH:17][C:16]2[C:11]3[C:10]4[CH2:27][CH2:28][N:7]([C:5](=[O:6])/[CH:4]=[CH:3]/[CH2:2][N:42]5[CH2:43][CH2:44][CH2:45][O:39][CH2:40][CH2:41]5)[CH2:8][C:9]=4[S:26][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 230902141,4-Oxazepane hydrochlorideHCID 581168067-[(2E)-4-Chlorobut-2-enoyl]-N-(3,4-dichlorophenyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 25221098N-(3,4-Dichlorophenyl)-7-[(2E)-4-(1,4-oxazepan-4-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 59A (100 mg, 0.201 mmol) in DMF (2 mL) and DIPEA (0.10 mL, 0.60 mmol) was added 1,4-oxazepane hydrochloride (55 mg, 0.40 mmol). The mixture was stirred for 1 h at rt and then heated for 1 h to 50° C. The reaction mixture was directly separated by preparative HPLC. The product crystallized upon trituration with dichloromethane. The solvent was removed in vacuo to yield 83 mg (80%) of the title compound.

Workup

  1. temperatureheated for 1 h to 50° C
  2. customThe reaction mixture was directly separated by preparative HPLC
  3. customThe product crystallized upon trituration with dichloromethane
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b3e44f7de2ac454eb923f837fd3cbd88
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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