Hydrochloric Acid → HCID 54669956, compound

HRID 1404787Notes

Reaction equation

HRID 1404787 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21]5[CH:42]=[CH:41][C:24]([C:25]([NH:27][CH:28]6[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]6)=[O:26])=[CH:23][CH:22]=5)=[CH:19][CH:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[ClH:43]>C1COCC1.CCOCC>[ClH:43].[NH:31]1[CH2:32][CH2:33][CH:28]([NH:27][C:25](=[O:26])[C:24]2[CH:41]=[CH:42][C:21]([C:18]3[N:17]=[C:16]4[N:12]([CH2:11][C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[N:1]=[CH:2][CH:3]=[CH:4]6)[N:13]=[N:14][C:15]4=[CH:20][CH:19]=3)=[CH:22][CH:23]=2)[CH2:29][CH2:30]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54670043HCID 54670043, compound

Product 1

HCID 54669956HCID 54669956, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of example 29 (0.125 g, 0.222 mmol) in THF (1 ml), ether saturated with HCl (1.5 ml) was added at 0° C. and stirred for 15 min. The precipitate formed was washed with ether and dried under vacuum to afford the title compound as light yellow solid (0.105 g. 95%). M.P.: 220-224° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 9.14 (d, J=3.6 Hz, 1H), 8.90 (m, 3H), 8.72 (d, J=8.7 Hz, 1H), 8.67 (d, J=7.4 Hz, 1H), 8.33 (d, J=8.5 Hz, 2H), 8.28 (m, 3H), 8.11 (dd, J=8.7, 1.5 Hz, 1H), 8.05 (d, J=8.5 Hz, 2H), 7.89 (dd, J=8.3, 4.8 Hz, 1H), 6.29 (s, 2H), 4.11 (m, 1H), 3.59 (m, 1H), 3.34 (m, 1H), 3.01 (m, 2H), 1.99 (m, 2H), 1.85 (m, 2H).

Workup

  1. customThe precipitate formed
  2. washwas washed with ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-92be11ae55bd4dc0852647ee11873ec5
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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