Hydrochloric Acid → HCID 86639688, compound

HRID 1426147Notes

Reaction equation

HRID 1426147 reaction equation
[Br-].[CH3:2][N:3]([CH3:25])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH2:31]([O:38][C:39]1[C:40]([NH:47][C:48]2[S:49][CH:50]=[C:51]([CH3:53])[N:52]=2)=[N:41][CH:42]=[C:43]([CH:46]=1)[CH:44]=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[ClH:54]>C1COCC1>[ClH:54].[ClH:54].[CH2:31]([O:38][C:39]1[C:40]([NH:47][C:48]2[S:49][CH:50]=[C:51]([CH3:53])[N:52]=2)=[N:41][CH:42]=[C:43](/[CH:44]=[CH:5]/[CH2:4][N:3]([CH3:25])[CH3:2])[CH:46]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 16661007HCID 16661007, compoundHCID 178418339Butyllithium

Product 1

HCID 86639688HCID 86639688, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 25 mL round-bottomed flask was charged with [2-(dimethylamino)ethyl]triphenylphosphonium bromide (1114 mg, 2.69 mmol) and THF (5 mL). The reaction was cooled to 0° C. under nitrogen. Butyllithium (1.08 ml, 2.69 mmol) was added slowly and the reaction was stirred for 50 minutes. A solution of 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (350 mg, 1.08 mmol) in THF (5 mL) was added and the reaction was stirred at ambient temperature for 1.5 hours. The reaction was partitioned between EtOAc and water. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on a silica gel column (10 to 20% methanol in EtOAc with NH4OH) to afford the title compound (250 mg, 51.3% yield) after HCl salt formation. 1H NMR (DMSO-d6) δ 10.85 (bs, 1H), 10.49 (bs, 1H), 8.03 (d, 1H), 7.78 (s, 1H), 7.63 (d, 2H), 7.45-7.33 (m, 3H), 6.82 (m, 3H), 6.45 (m, 1H), 5.37 (s, 2H), 3.85 (m, 2H), 2.77 (d, 6H), 2.30 (s, 3H). Mass spectrum (apci) m/z=381.1 (M+H-2HCl).

Workup

  1. stirringthe reaction was stirred at ambient temperature for 1.5 hours
  2. customThe reaction was partitioned between EtOAc and water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a silica gel column (10 to 20% methanol in EtOAc with NH4OH)

Sources & evidence

ORD record
ord-06f244e4942c4db9bc08f69ce6c11fbb
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

Loading…