HCID 21923109, compound → HCID 58293025, compound

HRID 1947995Notes

Reaction equation

HRID 1947995 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[N:3]=1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([CH:33]2[CH2:38][CH2:37][CH:36]([P:39](=[O:46])([O:43][CH2:44][CH3:45])[O:40][CH2:41][CH3:42])[CH2:35][CH2:34]2)=[C:26]2[C:30]=1[C:29](=[O:31])[N:28]([CH3:32])[CH2:27]2>>[CH2:41]([O:40][P:39]([CH:36]1[CH2:37][CH2:38][CH:33]([C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:2]3[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[O:19][CH3:20])[N:3]=3)=[C:30]3[C:26]=2[CH2:27][N:28]([CH3:32])[C:29]3=[O:31])[CH2:34][CH2:35]1)(=[O:46])[O:43][CH2:44][CH3:45])[CH3:42]

Participants

3

Reactant 2

HCID 21923109HCID 21923109, compoundHCID 86654037HCID 86654037, compound2×

Product 1

HCID 58293025HCID 58293025, compound

Procedure

The title compound was prepared according to the procedure for Example 102 using 4-chloro-N-(2-methoxyphenyl)-5-(trifluoromethyl)pyrimidin-2-amine (7.2 mg, 0.024 mmol) and diethyl [4-(7-amino-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)cyclohexyl]phosphonate (Compound 193A, 9.0 mg, 0.024 mmol). The reaction mixture was purified by MDP (basic buffer) to give a white solid. The material was further purified by silica gel chromatography (ISCO Combi-flash system, eluting with 0-8% MeOH/DCM), affording the title compound as a white solid, 5 mg. (4:1 mixture, cis and trans unassigned). 1H NMR (CDCl3): 1.40 (t, J=7.1 Hz, 6H), 1.11 (t, J=7.6 Hz, 3H), 1.70-1.84 (m, 4H), 2.09-2.28 (m, 5H), 2.58 (m, 1H), 3.23 (s, 3H), 3.94, 3.95 (2xs, 3H), 4.14-4.23 (m, 4H), 4.39, 4.43 (2xs, 2H), 6.95-7.02 (m, 2H), 7.10 (m, 1H), 7.35 (d, J=8.6 Hz, 1H), 7.93 (m, 1H), 8.26 (m, 1H), 8.38 (s, 1H), 8.58 (d, J=8.3 Hz, 1H), 10.64 (s, 1H). MS (ES+): m/z=648.33 [MH+]. HPLC: tR=4.53 min (ZQ3, polar—5 min).

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was purified by MDP (basic buffer)
  3. customto give a white solid
  4. customThe material was further purified by silica gel chromatography (ISCO Combi-flash system, eluting with 0-8% MeOH/DCM)

Sources & evidence

ORD record
ord-074cd71a7f394fb0aacd0f3cbab436ba
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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