Acetone → 2-[5-Chloro-2-(12-isopropyl-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide

HRID 1040624Notes

Reaction equation

HRID 1040624 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]12[NH:26][CH:23]([CH2:24][CH2:25]1)[CH2:22][C:21]1[CH:20]=[CH:19][C:18]([NH:27][C:28]3[N:33]=[C:32]([NH:34][C:35]4[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=4[C:37]([NH:39][CH3:40])=[O:38])[C:31]([Cl:45])=[CH:30][N:29]=3)=[CH:17][C:16]2=1.[CH3:46][C:47]([CH3:49])=O.ClC(Cl)C>C(O)(=O)C>[Cl:45][C:31]1[C:32]([NH:34][C:35]2[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=2[C:37]([NH:39][CH3:40])=[O:38])=[N:33][C:28]([NH:27][C:18]2[CH:19]=[CH:20][C:21]3[CH2:22][CH:23]4[N:26]([CH:47]([CH3:49])[CH3:46])[CH:15]([CH2:25][CH2:24]4)[C:16]=3[CH:17]=2)=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 668293732-[2-(12-Aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzamide

Product 1

HCID 668295692-[5-Chloro-2-(12-isopropyl-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

Sodium triacetoxyborohydride (100 mg, 0.47 mmol) was added to a solution of 2-[2-(12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamino)-5-chloro-pyrimidin-4-ylamino]-N-methyl-benzamide (100 mg, 0.23 mmol), acetone (0.034 mL, 0.47 mmol), acetic acid (1 drop) and dichloroethane (5 mL). The reaction was stirred at room temperature for 18 h. The reaction was then quenched with saturated aqueous NaHCO3 (5 mL), extracted with CH2Cl2 (2×5 mL), dried over MgSO4, filtered, and concentrated to afford the title compound as off-white solid (89 mg, 82%). 1HNMR (400 MHz, DMSO-d6) δ 11.6 (s, 1H), 9.3 (s, 1H), 8.8-8.7 (m, 2H), 8.2 (s, 1H), 7.8 (d, 1H, J=7.8 Hz), 7.5 (appt t, 1H, J=8.1 Hz), 7.4 (d, 1H, J=8.6), 7.3 (s, 1H), 7.1 (appt t, 1H, J=7.6 Hz), 6.9 (d, 1H, J=8.3 Hz), 3.9 (m, 1H), 3.6 (m, 1H), 3.0 (dd, 1H, J=17.2, 4.6 Hz), 2.8 (d, 3H, J=4.3 Hz), 2.4 (m, 1H), 2.2 (d, 1H, J=17.2 Hz), 2.1-2.0 (m, 2H), 1.6 (m, 1H), 1.5 (m, 1H), 1.1 (d, 3H, J=5.9 Hz), 0.9 (d, 3H, J=5.9 Hz); MS (m/e) 477 (M+1); mp 202-205° C.

Workup

  1. customThe reaction was then quenched with saturated aqueous NaHCO3 (5 mL)
  2. extractionextracted with CH2Cl2 (2×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1822634ff86e4b479d6c9305d02b677d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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