MI-773 → SAR405838 (MI-773)

HRID 1896972Notes

Reaction equation

HRID 1896972 reaction equation
[CH3:1][C:2]([CH2:5][C@H:6]1[NH:10][C@@H:9]([C:11]([NH:13][CH:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)=[O:12])[C@H:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=2[F:28])[C@:7]21[C:37](=[O:38])[NH:36][C:30]1[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:29]2=1)([CH3:4])[CH3:3]>CO.O>[CH3:4][C:2]([CH2:5][C@@H:6]1[NH:10][C@@H:9]([C:11]([NH:13][CH:14]2[CH2:15][CH2:16][CH:17]([OH:20])[CH2:18][CH2:19]2)=[O:12])[C@H:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=2[F:28])[C@@:7]21[C:37](=[O:38])[NH:36][C:30]1[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:29]2=1)([CH3:1])[CH3:3]

Participants

3

Reactant 1

HCID 52938482MI-773

Product 1

HCID 53476877SAR405838 (MI-773)Yield 95%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

In an alternative procedure, MI-773 (77 mg) was dissolved in 15 mL MeOH/H2O (v/v=1:1). After 3 days, the needle crystals that had formed were collected, washed with cold MeOH/H2O (v/v=1:1) and dried in vacuum to give MI-77301 as the free amine (20 mg; >95% purity as determined by HPLC). 1H NMR (300 MHz, MeOH-d4): 7.49-7.55 (m, 1H), 7.25-7.31 (m, 1H), 7.10-7.16 (m, 1H), 6.82 (d, J=1.8 Hz, 1H), 6.50-6.71 (m, 1H), 6.49 (d, J=8.4 Hz, 1H), 4.32 (d, J=9.0 Hz, 1H), 4.09 (d, J=8.7 Hz, 1H), 3.57-3.69 (m, 1H), 3.49 (d, J=9.2 Hz, 1H), 3.46-3.57 (m, 1H), 1.83-2.07 (m, 3H), 1.68-1.80 (m, 1H), 1.54 (dd, J=9.0, 14.3 Hz, 1H), 1.12-1.45 (m, 5H), 0.80 (s, 9H). The absolute stereochemical configuration of MI-77301 was determined by X-ray analysis.

Workup

  1. customthe needle crystals that had formed
  2. customwere collected
  3. washwashed with cold MeOH/H2O (v/v=1:1)
  4. customdried in vacuum

Sources & evidence

ORD record
ord-9deeeb4483a945d8ab3bce0a1f5c24b7
Source dataset
uspto-grants-2013_08
Patent number
US08518984B2

Reaction notes

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