Methanol → HCID 15221541, compound

HRID 275425Notes

Reaction equation

HRID 275425 reaction equation
N[C@@H]1C2C=C(C#N)C=CC=2OC(C)(C)C1.[C:16]([C:18]1[CH:19]=[CH:20][C:21]2[O:26][C:25]([CH3:28])([CH3:27])[CH2:24][C@@H:23]([N:29]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[N:31]=[C:30]3[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:22]=2[CH:43]=1)#[N:17].CO>O>[C:16]([C:18]1[CH:19]=[CH:20][C:21]2[O:26][C:25]([CH3:28])([CH3:27])[CH2:24][C@H:23]([N:29]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[N:31]=[C:30]3[C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:22]=2[CH:43]=1)#[N:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 15221540HCID 15221540, compoundHCID 15448760HCID 15448760, compound

Product 1

HCID 15221541HCID 15221541, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from (S)-4-amino-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (compound of title F, Example 4) by the same procedure as described for (R)-1-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-benzopyran-4-yl)-1H-benzimidazole-2-carboxylic acid, ethyl ester in example 4, parts G-J. [a]D =-111° (c=0.5, MeOH). Microanalysis calculated for C20H16N3ClO2.0.3 H2O: C, 64.71; H, 4.51; N, 11.32, Cl, 9.55. Found: C, 65.08; H, 4.72; N, 10.76, Cl, 9.26. Further elution of the column also provided (R)-4-[3-Chloro-2-oxo-1(2H)-quinoxalinyl]-3,4-dihydro-2,2-dimethyl-2H-benzopyran-6-carbonitrile, m.p. 174°-175° C. [a]D =+92.1° (c=0.42, MeOH). Microanalysis calculated for C22H21N3O2.0.7 H2O: C, 68.10; H, 5.82; N, 10.83. Found: C, 68.07; H,5.55; N, 10.65.

Workup

  1. washFurther elution of the column also provided (R)-4-[3-Chloro-2-oxo-1(2H)-quinoxalinyl]-3,4-dihydro-2,2-dimethyl-2H-benzopyran-6-carbonitrile, m.p. 174°-175° C. [a]D =+92.1° (c=0.42, MeOH)

Sources & evidence

ORD record
ord-bf78a1b5744e45e6bcbaeea52d838820
Source dataset
uspto-grants-1995_02
Patent number
US05393771

Reaction notes

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