Formaldehyde → N-(3-(5-fluoro-1-methylindolin-6-yl)-1-(1-methylazetidin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

HRID 331066Notes

Reaction equation

HRID 331066 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]3=[N:10][CH:11]=[CH:12][C:13]([NH:14][S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])=[C:8]3[C:7]([C:24]3[CH:32]=[C:31]4[C:27]([CH2:28][CH2:29][N:30]4[CH3:33])=[CH:26][C:25]=3[F:34])=[CH:6]2)[CH2:2]1.C=O.[C:37]([BH3-])#N.[Na+]>C(Cl)Cl>[F:34][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:24]=1[C:7]1[C:8]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[NH:14][S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:17])=[O:16])[N:5]([CH:3]3[CH2:2][N:1]([CH3:37])[CH2:4]3)[CH:6]=1)[N:30]([CH3:33])[CH2:29][CH2:28]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 71090140N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

Product 1

HCID 71090287N-(3-(5-fluoro-1-methylindolin-6-yl)-1-(1-methylazetidin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide D34 (394 mg, 0.825 mmol) in DCM (5 mL) was added formaldehyde (0.307 mL, 4.13 mmol) and sodium cyanoborohydride (104 mg, 1.650 mmol). The final mixture was stirred at RT for 1 h. The mixture was passed through a SCX cartridge eluting with MeOH and followed by 2M ammonia in MeOH. The desired fractions were concentrated and further purified on normal phase silica eluting with 2M ammonia in MeOH and DCM (0-10%) to give the title compound (153 mg). LCMS (A): m/z (M+H)+ 492, C26H26FN5O2S requires 491 (acidic).

Workup

  1. washeluting with MeOH
  2. concentrationThe desired fractions were concentrated
  3. customfurther purified on normal phase silica eluting with 2M ammonia in MeOH and DCM (0-10%)

Sources & evidence

ORD record
ord-a3c8330bc6464f6aafe443a0e8ee780f
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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