Acetaldehyde → HCID 71143666, compound

HRID 627799Notes

Reaction equation

HRID 627799 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])=[CH:23][CH:22]=4)[N:19]=3)[N:14](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=1)[CH2:7]2.[CH:52](=O)[CH3:53].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCCl>[CH2:52]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([S:27]([CH:30]([CH3:31])[CH3:32])(=[O:29])=[O:28])=[CH:23][CH:22]=4)[N:19]=3)[NH:14][CH:13]=1)[CH2:7]2)[CH3:53]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 5049666Sodium triacetoxyborohydrideHCID 86676507HCID 86676507, compound

Product 1

HCID 71143666HCID 71143666, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7-amino-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one (63 mg, 0.09133 mmol) dissolved in DCE (5 mL) and acetaldehyde (5.6 μL, 0.10 mmol) then Na(OAc)3BH (38.72 mg, 0.1827 mmol) added at RT under N2. Reaction mixture stirred for 48 h then quenched by the addition of water. DCM added and layers separated. Organic phase dried and concentrated. Residue taken up in DCM (2 mL) under N2 and treated with triethylsilane (73 μL, 0.4566 mmol) then TFA (300 μL). Reaction mixture stirred overnight then concentrated. Residue purified by hplc to give the title compound; 1H NMR (400 MHz, DMSO) δ 1.20-1.26 (9H, m), 3.50 (1H, partly obsc sep), 5.38 (2H, s), 6.64-6.68 (2H, m), 6.85 (1H, d), 7.42 (1H, d), 8.00 (2H, d), 8.44 (1H, d), 8.51 (2H, d), 9.08 (1H, s), 12.31 (1H, s) ppm; MS (ES+) 476.0.

Workup

  1. customReaction mixture
  2. customthen quenched by the addition of water
  3. additionDCM added
  4. customlayers separated
  5. customOrganic phase dried
  6. concentrationconcentrated
  7. customReaction mixture
  8. stirringstirred overnight
  9. concentrationthen concentrated
  10. customResidue purified by hplc

Sources & evidence

ORD record
ord-a20aece4e4ec4051811256b55ec2900c
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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