Acetonitrile--water (1/1) → HCID 59384316, compound

HRID 2357072Notes

Reaction equation

HRID 2357072 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C@@:13]3([CH3:27])[CH2:17][O:16]C(C)(C)[N:14]3C(OC(C)(C)C)=O)=[N:10][N:9]=2)=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].[C:32](#N)[CH3:33].O>>[NH2:14][C@@:13]([C:11]1[S:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH2:8][CH2:32][CH3:33])=[C:3]([C:28]([F:31])([F:30])[F:29])[CH:4]=2)=[N:9][N:10]=1)([CH3:27])[CH2:17][OH:16]

Participants

3

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 136123834HCID 136123834, compound

Product 1

HCID 59384316HCID 59384316, compound

Procedure

The title compound was prepared from protected phenyl-thiadiazole 6a in 90% (579 mg) yield. HPLC retention time on a C8(2) column (30×50 mm, 3 μL) is 1.68 min with gradient 50-98% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase. MS (ESI, M+H+)=446.2; 1H NMR (400 MHz, DMSO-d6) δ 8.21 (dd, 1H, J=9.0 Hz, J=2.0 Hz), 8.15 (d, 1H, J=2.0 Hz), 7.45 (d, 1H, J=8.4), 4.21 (t, 2H, J=6.2 Hz), 3.74-3.85 (m, 3H), 1.68-1.77 (m, 5H), 1.25-1.45 (m, 12H), 0.849 (t, 3H, J=6.4).

Workup

  1. customyield

Sources & evidence

ORD record
ord-df4fbe5ba6f049598fe0b2339471821a
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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