Morpholine → HCID 25265751, compound

HRID 1529509Notes

Reaction equation

HRID 1529509 reaction equation
[O:1]=[S:2]1[C:10]2[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7]([N:18]3[CH2:23][CH2:22][N:21]4[CH:24]=[C:25]([C:27](O)=[O:28])[N:26]=[C:20]4[CH2:19]3)=[N:6][C:5]=2[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>CN(C)C=O>[N:39]1([C:27]([C:25]2[N:26]=[C:20]3[CH2:19][N:18]([C:7]4[N:8]=[C:9]([NH:11][CH:12]5[CH2:13][CH2:14][O:15][CH2:16][CH2:17]5)[C:10]5[S:2](=[O:1])[CH2:3][CH2:4][C:5]=5[N:6]=4)[CH2:23][CH2:22][N:21]3[CH:24]=2)=[O:28])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 58154225HCID 58154225, compound

Product 1

HCID 25265751HCID 25265751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

50 mg of 7-[5-oxo-4-(tetrahydropyran-4-ylamino)-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-2-yl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid (see 13.1) are placed in 2 ml dimethylformamide, then 66 μl diisopropylethylamine and 54.2 mg O-(7-azabenzotriazol-1-yl+N,N,N″,N″-tetramethyluronium hexafluorophosphate (HATU) are added. After 15 min a suspension of 11.4 mg morpholine in 300 μl dimethylformamide is added. The reaction mixture is stirred at ambient temperature until there is no further reaction, and the product is purified directly by preparative HPLC (method B). 40 mg of Example 48 are obtained as a solid. Analytical HPLC-MS (method D): RT=0.79 min.

Workup

  1. additionis added
  2. customno further reaction
  3. customthe product is purified directly by preparative HPLC (method B)

Sources & evidence

ORD record
ord-e02167b73685458cbd85337b8d9a6c22
Source dataset
uspto-grants-2015_07
Patent number
US09090626B2

Reaction notes

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