Ammonia → HCID 24852032, compound

HRID 2381068Notes

Reaction equation

HRID 2381068 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([O:30][CH3:31])=[CH:9][CH:10]=[C:11]3[C:16]=2[N:15]([CH2:17][CH:18]=O)[C:14](=[O:20])[CH:13]=[C:12]3[NH:21][C:22]2[C:27]([Cl:28])=[CH:26][N:25]=[CH:24][C:23]=2[Cl:29])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:33][NH:34][CH3:35].C(N(CC)CC)C.[BH4-].[Na+].N>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[CH:1]1([O:6][C:7]2[C:8]([O:30][CH3:31])=[CH:9][CH:10]=[C:11]3[C:16]=2[N:15]([CH2:17][CH2:18][N:34]([CH3:35])[CH3:33])[C:14](=[O:20])[CH:13]=[C:12]3[NH:21][C:22]2[C:23]([Cl:29])=[CH:24][N:25]=[CH:26][C:27]=2[Cl:28])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 4311764Sodium borohydrideHCID 86618123HCID 86618123, compound

Product 1

HCID 24852032HCID 24852032, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

Titanium (IV) isopropoxide (496 mg, 1.74 mmol) and 2-(8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde (400 mg, 0.87 mmol) were added sequentially to a solution of dimethylamine hydrochloride (144 mg, 1.74 mmol), triethylamine (176 mg, 1.74 mmol), and absolute ethanol (20 mL). After stirring overnight, sodium borohydride (50 mg, 1.3 mmol) was added. After an additional 3 h, the reaction was poured into aq. ammonia (30 mL) and then filtered—washing with dichloromethane. The filtrate was extracted with dichloromethane (50 mL×3). The combined extracts were dried, filtered, concentrated, and purified by reverse-phase HPLC to give 8-(cyclopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-1-(2-(dimethylamino)ethyl)-7-methoxyquinolin-2(1H)-one: 1H NMR (400 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.73 (s, 2H), 7.91 (d, 1H), 7.12 (d, 1H), 4.94 (s, 1H), 4.71 (t, 2H), 4.58 (m, 1H), 3.90 (s, 3H), 2.22 (m, 2H), 2.04 (s, 6H), 1.80-1.50 (m, 8H); MS (ESI): 491.0.

Workup

  1. waitAfter an additional 3 h
  2. washfiltered—washing with dichloromethane
  3. extractionThe filtrate was extracted with dichloromethane (50 mL×3)
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-aa46306b17664c7e80dda2ce2d4f44b6
Source dataset
uspto-grants-2012_09
Patent number
US08258154B2

Reaction notes

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