Dimethylformamide → HCID 56644633, compound

HRID 2066412Notes

Reaction equation

HRID 2066412 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[N:7]([CH3:33])[C:8]3[C:13]([N:14]=2)=[C:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:11]=[C:10]([N:21]2[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=[C:22]2[CH:30]([CH3:32])[CH3:31])[N:9]=3)[CH2:2]1.[CH3:34][C:35]1([O:38][CH2:37]1)[CH3:36].CN(C=O)C>O>[CH:30]([C:22]1[N:21]([C:10]2[N:9]=[C:8]3[C:13]([N:14]=[C:6]([O:5][CH:3]4[CH2:4][N:1]([CH2:34][C:35]([CH3:37])([OH:38])[CH3:36])[CH2:2]4)[N:7]3[CH3:33])=[C:12]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[N:11]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=1)([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11208Isobutylene oxideHCID 56645872HCID 56645872, compound

Product 1

HCID 56644633HCID 56644633, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 4-(8-(azetidin-3-yloxy)-2-(2-isopropyl-1H-benzo[d]imidazol-1-yl)-9-methyl-9H-purin-6-yl)morpholine (46.3 mg), isobutylene oxide (0.0183 mL), DMF (0.75 mL) and water (0.25 mL) was heated at 60° C. for 3 h. The contents were concentrated. Diluted aqueous Na2CO3 solution was added. The mixture was extracted with DCM (2×). The DCM extracts were dried with Na2SO4. The crude was purified with HPLC to give the product (17.2 mg). 1H NMR (400 MHz, CDCl3) δ 7.83 (dd, J=6.9, 2.0 Hz, 1H), 7.77 (dd, J=6.8, 1.9 Hz, 1H), 7.25-7.20 (m, 2H), 5.41 (p, J=5.8 Hz, 1H), 4.21 (s, 4H), 3.95 (ddd, J=20.5, 14.5, 7.9 Hz, 3H), 3.87-3.79 (m, 4H), 3.61 (s, 3H), 3.48-3.37 (m, 2H), 2.56 (s, 2H), 1.44 (d, J=6.8 Hz, 6H), 1.17 (s, 6H). LCMS: M+H+=521.3.

Workup

  1. concentrationThe contents were concentrated
  2. additionDiluted aqueous Na2CO3 solution was added
  3. extractionThe mixture was extracted with DCM (2×)
  4. dry with materialThe DCM extracts were dried with Na2SO4
  5. customThe crude was purified with HPLC

Sources & evidence

ORD record
ord-a2096653d37d4e459cc5cf463c0b96e2
Source dataset
uspto-grants-2012_10
Patent number
US08293736B2

Reaction notes

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