Acetic Acid → HCID 42638722, compound

HRID 2280019Notes

Reaction equation

HRID 2280019 reaction equation
[CH:1]1([N:6]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:34]=[CH:33][C:23]([C:24]([NH:26][CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[O:25])=[CH:22][C:21]=4[O:35][CH3:36])=[N:18][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:51]1[CH2:56][CH2:55][C:54](=O)[CH2:53][CH2:52]1.C(O)(=O)C>C(Cl)Cl>[CH:1]1([N:6]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:34]=[CH:33][C:23]([C:24]([NH:26][CH:27]5[CH2:32][CH2:31][N:30]([CH:54]6[CH2:55][CH2:56][O:51][CH2:52][CH2:53]6)[CH2:29][CH2:28]5)=[O:25])=[CH:22][C:21]=4[O:35][CH3:36])=[N:18][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-one2×HCID 5049666Sodium triacetoxyborohydride2×HCID 25007869HCID 25007869, compound2×

Product 1

HCID 42638722HCID 42638722, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(9-Cyclopentyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(piperidin-4-yl)benzamide (Intermediate 12) (35 mg, 0.07 mmol, 1 eq) and sodium triacetoxyborohydride (18 mg, 0.084 mmol, 1.2 eq) in DCM (0.5 mL) were reacted with tetrahydropyran-4-one (6.5 μL, 0.07 mmol, 1 eq) at rt for 2 days. Further and sodium triacetoxyborohydride (18 mg, 1.2 eq), tetrahydropyran-4-one (6.5 μL, 1 eq) were added and acetic acid (4 μL, 1 eq). After two days the RM was diluted with DCM, washed with water and the organic layer concentrated in vacuo. The resulting residue was purified by preparative RP-HPLC-MS (Preparative 1) to provide 4-(9-cyclopentyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-[1-(tetrahydro-pyran-4-yl)-piperidin-4-yl]-benzamide (10 mg, 25%).

Workup

  1. washwashed with water
  2. concentrationthe organic layer concentrated in vacuo
  3. customThe resulting residue was purified by preparative RP-HPLC-MS (Preparative 1)

Sources & evidence

ORD record
ord-03b120c8e27644ca85f637736d14d31d
Source dataset
uspto-grants-2015_09
Patent number
US09133199B2

Reaction notes

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