Dimethylformamide → HCID 66678956, compound

HRID 1626642Notes

Reaction equation

HRID 1626642 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][NH:21][CH2:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.CN(C=O)C.[O:42]1[CH2:47][CH2:46][CH:45]([C:48](Cl)=[O:49])[CH2:44][CH2:43]1>C(Cl)Cl>[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]4[CH3:29])[C:17]4[CH2:22][N:21]([C:48]([CH:45]5[CH2:46][CH2:47][O:42][CH2:43][CH2:44]5)=[O:49])[CH2:20][C:18]=4[N:19]=3)=[CH:12][CH:13]=2)=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2795505Oxane-4-carbonyl chlorideHCID 46894114(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea

Product 1

HCID 66678956HCID 66678956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (Example 3) (100 mg, 0.37 mmol) and triethyamine (42.4 μL, 0.30 mmol) in DCM (3 mL, anhydrous), and DMF (1 mL, anhydrous) was added tetrahydro-2H-pyran-4-carbonyl chloride (45.2 mg, 0.30 mmol). The reaction mixture was stirred at room temperature until LCMS indicated reaction was complete. Solvent was then removed in vacuo.

Workup

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  2. customSolvent was then removed in vacuo

Sources & evidence

ORD record
ord-33da156e8a4b4614b3f5fe0431ca7eb3
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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