Hydrochloric Acid → HCID 86298673, compound

HRID 2279453Notes

Reaction equation

HRID 2279453 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:19][C:20]([N:22]1[CH2:31][CH2:30][C:29]2[CH:28]=[N:27][C:26]([NH:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[N:25][C:24]=2[CH2:23]1)=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=1)(C(C)(C)C)(C)C.Cl.[NH4+].[Cl-]>CO.C(Cl)Cl>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C@H:10]([NH:19][C:20]([N:22]2[CH2:31][CH2:30][C:29]3[CH:28]=[N:27][C:26]([NH:32][CH:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[N:25][C:24]=3[CH2:23]2)=[O:21])[CH2:9][OH:8])=[CH:12][C:13]=1[F:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 68294420HCID 68294420, compound

Product 1

HCID 86298673HCID 86298673, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 70 (1.236 g, 2.191 mmol) in 15% MeOH/DCM (75 mL) was added slowly HCl (2.19 mL, 8.763 mmol) and the reaction was stirred at RT for 20 min. Saturated NH4Cl was added slowly and the resulting solution extracted with DCM. The organic layer was separated and concentrated. The crude residue was purified by SiO2 chromatography eluting with an MeOH/DCM gradient (4 to 5% MeOH) to afford 0.841 g (85.3%) of I-14: 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.38 (t, 1H), 7.14 (dd, 1H), 7.08 (d, 1H), 5.28 (d, 1H), 4.97 (m, 1H), 4.89 (d, 1H), 4.39 (s, 2H), 4.06-3.90 (m, 4H), 3.86 (m, 1H), 3.76-3.60 (m, 2H), 3.55 (dt, 2H), 2.69 (t, 2H), 2.26 (t, 1H), 2.02 (d, 2H), 1.53 (m, 2H); LCMS (ACPI-pos) m/z 450.0 (M+H)+.

Workup

  1. extractionthe resulting solution extracted with DCM
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customThe crude residue was purified by SiO2 chromatography
  5. washeluting with an MeOH/DCM gradient (4 to 5% MeOH)
  6. customto afford 0.841 g (85.3%) of I-14

Sources & evidence

ORD record
ord-2763e8301b554016a6f5e54370dbd136
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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