Hydrochloric Acid → HCID 90412418, compound

HRID 1521964Notes

Reaction equation

HRID 1521964 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[NH:34][C:20]3=[N:21][CH:22]=[CH:23][C:24]([C:25]4[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=4[O:32][CH3:33])=[C:19]3[CH:18]=2)[CH2:12]1)(C(C)(C)C)(C)C.CO.Cl>ClCCl>[F:31][C:29]1[CH:28]=[CH:27][C:26]([O:32][CH3:33])=[C:25]([C:24]2[CH:23]=[CH:22][N:21]=[C:20]3[NH:34][C:17]([CH:13]4[CH2:14][CH2:15][CH2:16][N:11]([CH2:10][CH2:9][OH:8])[CH2:12]4)=[CH:18][C:19]=23)[CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 90412236HCID 90412236, compound

Product 1

HCID 90412418HCID 90412418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 128A (80 mg, 0.16 mmol)) in dichloromethane (2 mL) and methanol (2 mL) was treated with 37% hydrochloric acid (0.1 mL) for 10 minutes and concentrated. The residue was purified by reverse phase HPLC, and was eluted with 10-70% acetonitrile in 0.1% trifluoroacetic acid/water to afford the title compound. LCMS: 370.20 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 1.56-1.69 (m, 1H) 1.83-2.01 (m, 2H) 2.16 (d, 1H) 2.85-2.99 (m, 1H) 3.14-3.23 (m, 3H) 3.26-3.40 (m, 2H) 3.74 (s, 3H) 3.75-3.80 (m, 2H) 6.11 (d, 1H) 7.09 (d, 1H) 7.18-7.24 (m, 2H) 7.25-7.32 (m, 1H) 8.22 (d, 1H) 9.55 (s, 1H) 11.88 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reverse phase HPLC
  3. washwas eluted with 10-70% acetonitrile in 0.1% trifluoroacetic acid/water

Sources & evidence

ORD record
ord-edd0b64a92ef45558171e0130458ad76
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…