Triisopropyl phosphite → HCID 178478281, compound

HRID 75211

Reaction equation

HRID 75211 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[C:8]1[N:9](O)[C:10]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]3[N:21]=[CH:22][CH:23]=[CH:24][C:12]=3[C:11]=2[N:25]=1.P(OC(C)C)(OC(C)C)OC(C)C>CN(C)C(=O)C.C(#N)C.O>[Cl:27][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]1[NH:9][C:10]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13]3[N:21]=[CH:22][CH:23]=[CH:24][C:12]=3[C:11]=2[N:25]=1

Participants

6

Reactant 2

HCID 8304Triisopropyl phosphiteHCID 668869862-(3,5-dichloropyridin-4-yl)imidazo[4,5-d]dipyrido[2,3-b:3',4'-f]azepin-3(8H)-ol

Product 1

HCID 178478281HCID 178478281, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

The crude product from above, 2-(3,5-dichloropyridin-4-yl)imidazo[4,5-d]dipyrido[2,3-b:3′,4′-f]azepin-3(8H)-ol, (0.416 mmol, Intermediate D-8) was dissolved in N,N-dimethylacetamide (1.50 mL) and triisopropyl phosphite (0.19 mL, 0.83 mmol) and heated to 160° C. for 1 h. The mixture was cooled to room temperature, then diluted with acetonitrile and water and the product isolated by preparative HPLC. The pure fractions were combined, concentrated, and then lyophilized to provide the desired product as a yellow powder. 1H NMR (DMSO-d6, 2 tautomers) δ 13.01 (bs, 1H), 8.84 (s, 2H), 8.65 and 8.52 (bs, 1H), 8.42 and 8.15 (bs, 1H), 7.98 (m, 1H), 7.87 (m, 1H), 7.75 and 7.44 (d, 1H), 6.81 (m, 2H). LC/MS: 381, 383 (M+H)+.

Workup

  1. customthe product isolated by preparative HPLC
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ea4693b008a44de7891260c6aeea6471
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Linked notes

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