Water → HCID 66970463, compound

HRID 1363166Notes

Reaction equation

HRID 1363166 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20](SC#N)[C:19]([N+:25]([O-:27])=[O:26])=[CH:18][N:17]=1.Cl.[F:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[O:42][CH2:41][CH2:40][C@H:39]2[NH2:46].O>CS(C)=O.CCN(C(C)C)C(C)C>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20]([NH:46][C@H:39]2[C:38]3[C:43](=[CH:44][CH:45]=[C:36]([F:35])[CH:37]=3)[O:42][CH2:41][CH2:40]2)[C:19]([N+:25]([O-:27])=[O:26])=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 566052112-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanateHCID 56973615(4R)-6-Fluoro-3,4-dihydro-2H-1-benzopyran-4-amine--hydrogen chloride (1/1)

Product 1

HCID 66970463HCID 66970463, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile (139 mg) in anhydrous DMSO (3 mL) was added to solution of (R)-6-fluorochroman-4-amine hydrochloride (79 mg) in anhydrous DMSO (3 mL) and DIEA (0.21 mL), the resulting dark red solution was stirred at RT under an atmosphere of Ar over which time the solution lighten to yellow. Upon completion of the reaction, the mixture was cooled to 0° C. with an ice bath, and water (25 mL) was added (exotherm). The resulting yellow solid was collected via filtration, washed with additional water, air dried, then dissolved in CH2Cl2, the organic solution was dried (MgSO4), filtered and evaporated to yield the titled compound (quant.), NMR CDCl3 1H δ 9.0 (s, 1H), 8.6 (d, 1H), 7.7 (br s, 1H), 7.4 (dd, 1H), 7.1 (d, 1H), 7.0-6.8 (m, 4H), 6.5-6.4 (m, 2H), 5.2 (br s, 1H), 4.3 (s, 2H), 4.2 (br s, 2H), 3.8 (s, 6H), 2.2 (br s, 1H), 1.8 (br s, 1H); 19F δ −123 ppm; MH+=572.

Workup

  1. customUpon completion of the reaction
  2. temperaturethe mixture was cooled to 0° C. with an ice bath
  3. filtrationThe resulting yellow solid was collected via filtration
  4. washwashed with additional water, air
  5. customdried
  6. dissolutiondissolved in CH2Cl2
  7. dry with materialthe organic solution was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-715d131c146846e9bc10041bde7b82be
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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