Formaldehyde → HCID 25124329, compound

HRID 1945138Notes

Reaction equation

HRID 1945138 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([CH3:14])([CH3:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:34]=[CH:33][C:25]([C:26]([NH:28][CH:29]5[CH2:32][NH:31][CH2:30]5)=[O:27])=[CH:24][C:23]=4[O:35][CH3:36])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[C:39]([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO.Cl>[CH:1]1([N:6]2[CH2:12][C:11]([CH3:13])([CH3:14])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:34]=[CH:33][C:25]([C:26]([NH:28][CH:29]5[CH2:32][N:31]([CH3:39])[CH2:30]5)=[O:27])=[CH:24][C:23]=4[O:35][CH3:36])=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 67392355HCID 67392355, compound

Product 1

HCID 25124329HCID 25124329, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

4-(9-cyclopentyl-6,7,8,9-tetrahydro-5,7,7-trimethyl-6-oxo-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-N-(azetidin-3-yl)-3-methoxybenzamide (69 mg, 0.14 mmol) was dissolved in methanol (1.5 ml). 37% aqueous formaldehyde (66 μl, 0.84 mmol) and sodium cyanoborohydride (26 mg, 0.42 mmol) were successively added. The reaction mixture was stirred at room temperature for 2 hours. The crude mixture was diluted with 2N HCl then, basified with a saturated solution of NaHCO3. The mixture was extracted twice with ethyl acetate. The combined organic phases were dried (MgSO4 and concentrated in vacuo. The title compound (33 mg) was obtained as a white solid after crystallization from ethyl acetate. NMR DMSO D6 1.10 (6H, s), 1.55-1.69 (4H, m), 1.69-1.80 (2H, m), 1.82-1.95 (2H, m), 2.28 (3H, s), 3.01 (2H, t), 3.38 (2H, s), 3.57 (2H, t), 3.95 (3H, s), 4.39-4.50 (1H, m), 5.12-5.25 (1H, m), 7.43-7.52 (2H, m), 7.71 (1H, s), 8.00 (1H, s), 8.38 (1H, d), 8.63 (1H, d); HPLC rt(min): 9.60; MS (ES+) 508, (ES−) 506.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried (MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c8c178365fe4f6d80d973495b3efa56
Source dataset
uspto-grants-2013_03
Patent number
US08394952B2

Reaction notes

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