Carbonate Ion → HCID 57635045, compound

HRID 2111302Notes

Reaction equation

HRID 2111302 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([N:14]2[CH2:20][CH:19]([CH3:21])[C:18](=[O:22])[NH:17][C:16]3[CH:23]=[N:24][C:25]([NH:27][C:28]4[CH:43]=[CH:42][C:31]([C:32]([NH:34][CH:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)=[O:33])=[CH:30][C:29]=4[O:44][CH3:45])=[N:26][C:15]2=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-]>O1CCCC1>[CH:8]1([N:14]2[CH2:20][CH:19]([CH3:21])[C:18](=[O:22])[NH:17][C:16]3[CH:23]=[N:24][C:25]([NH:27][C:28]4[CH:43]=[CH:42][C:31]([C:32]([NH:34][CH:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)=[O:33])=[CH:30][C:29]=4[O:44][CH3:45])=[N:26][C:15]2=3)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 19660Carbonate IonHCID 68907722HCID 68907722, compound

Product 1

HCID 57635045HCID 57635045, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.045 g of (rac)-4-(9-cyclohexyl-7-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide trifluoro-acetic acid salt in tetrahydrofuran was added 0.2 g of SilicaBond Carbonate (Silicycle). The mixture was stirred at room temperature for 3 hours, then filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with dichloromethane-methanol (100:0-75:25) to give 0.020 g of (rac)-4-(9-cyclohexyl-7-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (I-18) as a white powder. HRMS (ES+) m/z Calcd for C28H39N7O3+H [(M+H)+]: 522.3187. Found: 522.3187.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with dichloromethane-methanol (100:0-75:25)

Sources & evidence

ORD record
ord-5d425e4da72e48188984099f11585ae2
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

Loading…