Formaldehyde → HCID 24803236, compound

HRID 1851739Notes

Reaction equation

HRID 1851739 reaction equation
C=O.F[C:4](F)(F)C(O)=O.[N:10]1([C:16]2[N:21]=[CH:20][C:19]([C:22]3[S:23][C:24]4[CH:30]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:18][CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C([BH3-])#N.[Na+]>CO>[CH3:4][N:13]1[CH2:12][CH2:11][N:10]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[S:23][C:24]4[CH:30]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:18][CH:17]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67276893HCID 67276893, compound

Product 1

HCID 24803236HCID 24803236, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Formaldehyde (37% aq., 0.212 mL, 2.61 mmol) was added to a suspension of ethyl 2-(6-piperazin-1-ylpyridin-3-yl)-1,3-benzothiazole-6-carboxylate trifluoroacetate (0.315 g, 0.65 mmol) in methanol (10 mL). Sodium cyanoborohydride (74 mg, 1.17 mmol) was added and the resulting mixture was stirred at r.t. for 1 h. The r.m. was then kept at −10° C. o.n. The formed solid was collected, washed with cold methanol and dried to give the title compound. The mother liquor was evaporated in vacuo and the residue was partitioned between DCM and sat. sodium hydrogencarbonate. The aqueous layer was extracted twice with DCM, dried (Na2SO4), filtered, and evaporated in vacuo, giving together with the filtrated solid the title compound (0.20 g) as a yellow solid. 1H NMR δ ppm 8.83 (d, 1 H) 8.73 (s, 1 H) 8.17 (dd, 1 H) 8.05 (s, 2 H) 7.01 (d, 1 H) 4.36 (q, 2 H) 3.70 (br. s., 4 H) 3.32 (s, 4 H) 2.29 (s, 3 H) 1.36 (t, 3 H); MS m/z (M+H) 383.

Workup

  1. customwas then kept at −10° C.
  2. customThe formed solid was collected
  3. washwashed with cold methanol
  4. customdried

Sources & evidence

ORD record
ord-993cddafbf1249f08913f3f2b8780429
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

Loading…