Acetonitrile → HCID 44624306, compound

HRID 420295Notes

Reaction equation

HRID 420295 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:38]=[CH:39][CH:40]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([F:27])[C:24]([NH:28][C:29](=[O:34])[CH2:30][NH:31][CH2:32][CH3:33])=[C:23]([CH2:35][CH3:36])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11]C1=O)([CH3:4])([CH3:3])[CH3:2].C(#N)C>O>[C:1]([C:5]1[CH:6]=[C:7]([CH:38]=[CH:39][CH:40]=1)[CH2:8][NH:9][C@H:17]1[CH2:16][S:15](=[O:18])(=[O:19])[CH2:14][C@@H:13]([CH2:20][C:21]2[CH:26]=[C:25]([F:27])[C:24]([NH:28][C:29](=[O:34])[CH2:30][NH:31][CH2:32][CH3:33])=[C:23]([CH2:35][CH3:36])[CH:22]=2)[C@@H:12]1[OH:11])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 131729373HCID 131729373, compound

Product 1

HCID 44624306HCID 44624306, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared in analogous manner as described for example 1o from N-{4-[(3aR,7S,7aS)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-ethyl-6-fluoro-phenyl}-2-ethylamino-acetamide to yield after preparative HPLC (Sunfire C18 OBD 5 μm, 100×30, 5-50% ACN in water+0.1% TFA gradient, 25 min) the title compound as a light yellow amorphous solid: UPLC RtD=1.084 min; ESIMS [M+H]+=548; 1H NMR (600 MHz, DMSO-d6+TFA): δ 9.96 (s, 1H), 9.70 (s, 1H), 9.0 (s, 1H), 8.90 (s, 1H), 7.63 (s, 1H), 7.44 (m, 1H), 7.37 (m, 1H), 6.98 (d, 1H), 6.95 (s, 1H), 4.26 (m, 2H), 4.02 (m, 2H), 3.84 (d, 1H), 3.66 (dd, 1H), 3.61 (dd, 1H), 3.1-3.3 (m (3H), 3.0 (m, 2H), 2.78 (d, 1H), 2.50 (m, 3H), 2.11 (m, 1H), 1.26 (s, 9H), 1.19 (t, 3H), 1.10 (t, 3H).

Workup

  1. customThe title compound was prepared in analogous manner

Sources & evidence

ORD record
ord-994a8c093423452a84bfe46f33c9d7da
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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