Dimethylamine → HCID 9956151, compound

HRID 396182Notes

Reaction equation

HRID 396182 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[C:5]([N:7]1[C:12]2=[CH:13][C:14]3[C:15]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[C:26]([Cl:31])[CH:25]=4)=[C:16]([C:21]#[N:22])[CH:17]=[N:18][C:19]=3[CH:20]=[C:11]2[O:10][CH2:9][CH2:8]1)=[O:6].BrC/C=C/[C:36]([N:38]1C2=CC3C(NC4C=CC(F)=C(Cl)C=4)=C(C#N)C=NC=3C=C2OC[CH2:39]1)=O.C(N(CC)C(C)C)(C)C.CNC.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[Cl:31][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[F:30])[NH:23][C:15]1[C:14]2[CH:13]=[C:12]3[N:7]([C:5](=[O:6])/[CH:4]=[CH:3]/[CH2:2][N:38]([CH3:39])[CH3:36])[CH2:8][CH2:9][O:10][C:11]3=[CH:20][C:19]=2[N:18]=[CH:17][C:16]=1[C:21]#[N:22]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10139225HCID 10139225, compoundHCID 10141819HCID 10141819, compound

Product 1

HCID 9956151HCID 9956151, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

An amount of the mixture 1-[(2E)-4-chloro-2-butenoyl]-9-(3-chloro-4-fluoroanilino)-2,3-dihydro-1H-[1,4]oxazino[3,2-g]quinoline-8-carbonitrile and 1-[(2E)-4-bromo-2-butenoyl]-9-(3-chloro-4-fluoroanilino)-2,3-dihydro-1H-[1,4]oxazino[3,2-g]quinoline-8-carbonitrile (0.708 g, 1.458 mmol), was dissolved in N,N-dimethylformamide (1.89 mL), and to this was added N,N-diisopropylethylamine (0.303 mL, 1.75 mmol), and 0.875 mL (1.75 mmol) of a 2.0 M solution of dimethylamine in tetrahydrofuran The reaction mixture was stirred for one hour, stored for 16 hours in the refrigerator, and then stirred with saturated sodium bicarbonate solution and brine. The solid was filtered off and washed with acetone to give a beige product (372 mg, 52% yield); m.p. 199-200° C.; 1H NMR (DMSO-d6) δ 9.70 (bs, 1H), 8.52 (s, 1H), 8.44 (bs, 1H), 7.47-7.37 (m, 3H), 7.25-7.23 (m, 1H), 6.86-6.79 (m, 1H), 6.62-6.57 (d, 1H), 4.44 (t, 2H), 4.06 (t, 2H), 3.02 (d, 2H), 2.06 (s, 6H); HRMS (Cl) m/z 466.1440 (M+1). Analysis for C24H21ClFN5O2.1.4H2O: Found: C, 60.48; H, 4.85; N, 14.49; F, 4.02; Cl, 7.52. Calcd: C, 60.28; H, 4.73; N, 14.66; F, 3.98; Cl, 7.32.

Workup

  1. waitstored for 16 hours in the refrigerator
  2. filtrationThe solid was filtered off
  3. washwashed with acetone

Sources & evidence

ORD record
ord-466073e0fbc844cc85d5231891da49ae
Source dataset
uspto-grants-2003_08
Patent number
US06608048B2

Reaction notes

Loading…