Acetic Acid → HCID 68510859, compound

HRID 1714036Notes

Reaction equation

HRID 1714036 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([O:35][CH3:36])=[O:34])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([NH:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[CH3:39]C(O)=O.C([BH3-])#N.[Na+].[OH-].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([O:35][CH3:36])=[O:34])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([N:27]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])[CH3:39])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 68511081HCID 68511081, compound

Product 1

HCID 68510859HCID 68510859, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude methyl 14-cyclohexyl-7-{[2-(dimethylamino)ethyl]amino}-3-fluoro-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (from Step 5) in DCM (0.05 M) was added formaldehyde (3.0 eq) and HOAc (5.5 eq), followed by sodium cyanoborohydride (3 eq). NaOH (20 eq, 1 N) was added after 2 h, and after stirring for 5 min the mixture was taken into EtOAc and washed with water and brine. Drying over Na2SO4 and concentration i. vac. gave the crude product which was used without further purification; MS (ES+) m/z 508 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialDrying over Na2SO4 and concentration i

Sources & evidence

ORD record
ord-1d43127f9b55452794090fdf0f56fa5f
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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