Trimethyl phosphite → Cyclopentylidene(6-methoxy-1H-indazol-3-yl)methyl dimethyl phosphate

HRID 229464Notes

Reaction equation

HRID 229464 reaction equation
Br[C:2]1([C:7]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[NH:11][N:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[P:20]([O:25]C)([O:23][CH3:24])[O:21][CH3:22]>>[P:20]([O:23][CH3:24])([O:21][CH3:22])([O:8][C:7](=[C:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1)[C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[NH:11][N:10]=1)=[O:25]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 68850204(1-bromocyclopentyl)(6-methoxy-1H-indazol-3-yl)methanone

Product 1

HCID 68850940Cyclopentylidene(6-methoxy-1H-indazol-3-yl)methyl dimethyl phosphate

Procedure

The title compound was prepared from (1-bromocyclopentyl)(6-methoxy-1H-indazol-3-yl)methanone and trimethyl phosphite using the procedure described in Method I Step B of Example 1 followed by RP-HPLC purification using 20-100% MeCN gradient. It was isolated as a white solid following lyophilization. 1H NMR (CDCl3, 500 MHz) δ 7.79 (d, 8.9 Hz, 1H), 6.85 (dd, 2.1 & 9.0 Hz, 1H), 6.81 (d, 1.8 Hz, 1H), 3.88 (s, 3H), 3.67 (d, 11.3 Hz, 6H), 2.72˜2.79 (m, 2H), 2.53˜2.59 (m, 2H), 1.70˜1.81 (m, 4H). LC-MS: 3.00 min. (n/Z=227.2, 353.2, 375.2).

Workup

  1. customfollowed by RP-HPLC purification
  2. customIt was isolated as a white solid following lyophilization
  3. custom3.00 min. (n/Z=227.2, 353.2, 375.2)

Sources & evidence

ORD record
ord-bd59ba3b2b204d7392e5f8c43357e2a3
Source dataset
uspto-grants-2009_07
Patent number
US07563816B2

Reaction notes

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