p-Toluenesulfonic acid → HCID 44599682, compound

HRID 1177548Notes

Reaction equation

HRID 1177548 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH:27]=O)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C([BH3-])#N.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.CO>[CH2:29]([NH:36][CH2:27][CH2:26][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:19][CH2:18]2)[N:11]=3)=[C:2]([F:1])[CH:3]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 86638722HCID 86638722, compound

Product 1

HCID 44599682HCID 44599682, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)acetaldehyde (44 mg, 0.113 mmol) was dissolved in chloroform (1.1 mL) before it was stirred at ambient temperature with benzylamine (62 μl, 0.57 mmol) and PTSA (1 mg) for 16 h. Methanol (1.1 mL) and sodium cyanoborohydride (7.1 mg, 0.113 mmol) were then added and allowed to stir in the reaction mixture over 3 d. The reaction mixture was diluted with DCM, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give the title compound after flash chromatography. MS (ESI) m/z: Calculated: 479.2; Observed: 480.1 (M++H).

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. washwashed with sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-ad78e595aee64e0e96e46ec8d40444a8
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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