Hydrochloric Acid → HCID 86639686, compound

HRID 1426143Notes

Reaction equation

HRID 1426143 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:11][CH:12]=[C:13]([CH:16]=1)[CH:14]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)(O)[O-].[Na+].[ClH:49]>C1COCC1>[ClH:49].[ClH:49].[CH2:1]([O:8][C:9]1[C:10]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:11][CH:12]=[C:13]([CH2:14][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 16661007HCID 16661007, compound

Product 1

HCID 86639686HCID 86639686, compoundYield 70.49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 20 mL vial was charged with 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (100 mg, 0.31 mmol) and THF (3 mL). morpholine (0.032 ml, 0.37 mmol) was added and the reaction was stirred for 10 minutes. NaBH(OAc)3 (326 mg, 1.54 mmol) was added and the reaction was stirred for 30 minutes. The reaction was poured into saturated sodium bicarbonate and extracted with EtOAc. The organic layer was washed with water and brine and then dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel (0 to 10% methanol in EtOAc containing ammonia) to afford the title compound (101.7 mg, 70.49% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 11.77 (bs, 1H), 11.05 (bs, 1H), 8.08 (m, 2H), 7.64 (d, 2H), 7.45-7.32 (m, 3H), 6.83 (s, 1H), 5.35 (s, 2H), 4.32 (d, 2H), 3.87 (m, 4H), 3.20 (d, 2H), 3.03 (m, 2H), 2.31 (s, 3H). Mass spectrum (apci) m/z=397.1 (M+H-2HCl).

Workup

  1. stirringthe reaction was stirred for 30 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel (0 to 10% methanol in EtOAc containing ammonia)

Sources & evidence

ORD record
ord-f258f08b23fe48f9a9093081ecadda44
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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