Formaldehyde → HCID 67449675, compound

HRID 1853754Notes

Reaction equation

[ClH:1].C[O:3][C:4]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3[S:15][CH:16]=[CH:17][C:7]=3[C:6]=2[C:5]=1[C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([CH3:28])[CH2:25][NH:26][CH3:27])=[CH:20][CH:19]=1.[CH2:29]=O>>[ClH:1].[CH3:29][N:26]([CH3:27])[CH2:25][C@@H:24]([C:21]1[CH:22]=[CH:23][C:18]([C:5]2[C:6]3[C:7]4[CH:17]=[CH:16][S:15][C:8]=4[C:9](=[O:14])[NH:10][C:11]=3[CH:12]=[CH:13][C:4]=2[OH:3])=[CH:19][CH:20]=1)[CH3:28]

Participants

Reactant 2

HCID 712Formaldehyde

HCID 67462257HCID 67462257, compound

Product 1

HCID 67449675HCID 67449675, compoundYield 67%

Procedure

Following the procedure outlined for Example 1387, (R)-8-methoxy-9-(4-(1-(methylamino)propan-2-yl)phenyl)thieno[2,3-c]quinolin-4(5H)-one hydrochloride (40 mg, 0.11 mmol) was reacted with paraformaldehyde (7 mg, 0.21 mmol) and after purification the resulting material was converted to the hydrochloride salt as outlined in General Procedure D-2 to afford the desired product (28 mg, 67%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.65-7.52 (m, 3H), 7.44-7.32 (m, 3H), 7.18 (d, J=8.9 Hz, 1H), 6.12 (d, J=5.4 Hz, 1H), 3.62 (d, J=3.1 Hz, 1H), 3.46 (dd, J=13.2, 4.7 Hz, 2H), 2.97 (s, 3H), 2.94 (s, 3H), 1.49 (d, J=6.6 Hz, 3H); ESI MS m/z 379 [C22H22N2O2S+H]+; HPLC >99% (AUC), tR=8.57 min.

Workup

customafter purification the resulting material

Sources & evidence

ORD record: ord-302b941139f0429f9c3682fe0d39c54d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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