Hydrochloric Acid → HCID 67450438, compound

HRID 1853893Notes

Reaction equation

HRID 1853893 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:31]=[CH:30][C:20]([CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:19][CH:18]=1)#[N:2].[ClH:32]>>[ClH:32].[NH2:22][CH2:21][C:20]1[CH:30]=[CH:31][C:17]([C:4]2[C:5]3[C:6]4[CH:16]=[CH:15][S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[C:1]#[N:2])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86689557HCID 86689557, compound

Product 1

HCID 67450438HCID 67450438, compoundYield 74%

Procedure

Following General Procedure D-3, tert-butyl 4-(8-cyano-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (10 mg, 0.023 mmol) was reacted with 4 N HCl (3 mL) to afford the desired product (7.4 mg, 74%) as a dark brown solid: 1H NMR (500 MHz, CD3OD) δ 7.89 (d, J=8.6 Hz, 1H), 7.74 (t, J=9.5 Hz, 2H), 7.65 (dd, J=14.4, 7.0 Hz, 2H), 7.55-7.53 (m, 2H), 6.08 (d, J=5.4 Hz, 1H), 4.32 (s, 2H); ESI MS m/z 330 [C19H13N3OS−H]−; HPLC 98.3% (AUC), tR=9.36 min.

Sources & evidence

ORD record
ord-b9d36222894d4a478c1e768d45121aac
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

Loading…