Trifluoroacetic acid → HCID 10189604, compound

HRID 1278775Notes

Reaction equation

HRID 1278775 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].O=[C:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([N:33]3[CH2:38][CH2:37][N:36]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:35][CH2:34]3)(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.C(C(O)=O)(F)(F)F>C(Cl)Cl>[OH:4][C@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[CH2:2][NH:1][CH:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:25]=[CH:26][C:27]([S:30]([N:33]3[CH2:34][CH2:35][N:36]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:37][CH2:38]3)(=[O:32])=[O:31])=[CH:28][CH:29]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 22713404HCID 22713404, compound

Product 1

HCID 10189604HCID 10189604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from N-{5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide and ethyl 2-(4-{[4-(4-oxo-1-piperidinyl)phenyl]sulfonyl}-1-piperazinyl)acetate in substantially the same manner, as described in Example 50. The product was obtained as a light yellow solid; mp: 91-92° C.; 1H NMR (400 MHz, DMSO-d6): δ 1.08-1.17 (t, 3H), 1.49-1.56 (m, 2H), 2.02-2.07 (m, 2H), 2.45-2.50 (m, 4H), 2.52-56 (m, 2H), 2.74-80 (m, 2H), 2.86-3.01 (m, 5H), 3.20 (s, 2H), 3.24-3.36 (m, 4H), 3.96-3.99 (d, 2H), 4.01-4.07 (q, 2H), 4.69-4.71 (m, 1H), 6.86-6.88 (d, 2H), 7.05-7.09 (m, 3H), 7.23-7.24 (m, 1), 7.47-7.50 (d, 2H), 8.20 (brs, 4H); MS m/z 640 (M+H)+; Analysis for C28H41N5O8S2×1.0 F3CCO2H×0.18 CH2Cl2 Calc'd: C, 47.13; H, 5.55; N, 9.11; Found: C, 47.02; H, 5.75; N, 8.67.

Workup

  1. customThe product was obtained as a light yellow solid

Sources & evidence

ORD record
ord-c956cedda34e41db9030403169ff952a
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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