Hydrochloric Acid → HCID 68223921, compound

HRID 1400941Notes

Reaction equation

HRID 1400941 reaction equation
[CH:1]1([NH:4][C:5](=[O:49])[NH:6][C:7]2[CH:47]=[CH:46][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:29]6[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30]6)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:48])[CH:8]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>C(Cl)Cl>[NH:31]1[CH2:30][CH:29]([N:28]([CH2:27][C:24]2[CH:25]=[N:26][C:21]([C:19]3[S:20][C:13]4[C:14](=[N:15][CH:16]=[CH:17][C:12]=4[O:11][C:10]4[CH:46]=[CH:47][C:7]([NH:6][C:5]([NH:4][CH:1]5[CH2:2][CH2:3]5)=[O:49])=[CH:8][C:9]=4[F:48])[CH:18]=3)=[CH:22][CH:23]=2)[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:32]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67443148HCID 67443148, compound

Product 1

HCID 68223921HCID 68223921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 431 (93 mg, 0.135 mmol) in DCM (5 mL) was added 4M HCl in 1,4-dioxane solution (0.17 mL, 0.675 mmol) and stirred at RT for 6 h. The mixture was then concentrated to afford the title compound 432 (presumably the hydrochloride salt) as beige solid which was used in the next step with no additional purification. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.13 (s, 1H), 8.98-8.86 (m, 1H), 8.78-8.66 (m, 1H), 8.69 (d, J=6.0 Hz, 1H), 8.63 (d, J=1.2 Hz, 1H), 8.40 (s, 1H), 8.34 (d, J=8.4 Hz, 1H), 7.94 (dd, J=8.0, 2.0 Hz, 1H), 7.77 (dd, J=13.6, 2.4 Hz, 1H), 7.44 (t, J=9.0 Hz, 1H), 7.25-7.21 (m, 1H), 6.92 (d, J=5.2 Hz, 1H), 6.77 (brs, 1H), 4.08 (q, J=7.2 Hz, 2H), 4.15-3.80 (m, 7H), 3.16 (s, 2H), 2.58-2.51 (m, 1H), 1.19 (t, J=7.2 Hz, 3H), 0.68-0.62 (m, 2H), 0.45-0.39 (m, 2H). MS (m/z): 591.58 (M+H).

Workup

  1. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-af2562756ecb4b019fe55488edfdeef8
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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