HCID 17768138, compound → HCID 58346672, compound

HRID 222056Notes

Reaction equation

HRID 222056 reaction equation
CN(/C=[C:5]1\[C:6](=O)[CH2:7][CH2:8][C:9]2[C:17]3[C:16]([O:18][CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=4)=[N:15][CH:14]=[N:13][C:12]=3[S:11][C:10]\1=2)C.C(O[C:36]([NH:38][NH:39][CH2:40][CH2:41][OH:42])=O)(C)(C)C>>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][O:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[C:17]=2[C:9]2[CH2:8][CH2:7][C:6]4[N:39]([CH2:40][CH2:41][OH:42])[N:38]=[CH:36][C:5]=4[C:10]=2[S:11]3)=[CH:22][CH:23]=1)([O-:29])=[O:28]

Participants

3

Reactant 2

HCID 17768138HCID 17768138, compoundHCID 58346746HCID 58346746, compound

Product 1

HCID 58346672HCID 58346672, compound

Procedure

This compound was prepared in a similar fashion as described in Example 80 starting from (8E)-8-[(dimethylamino)methylene]-4-[2-(4-nitrophenyl)ethoxy]-5,8-dihydro[1]benzothieno[2,3-d]pyrimidin-7(6H)-one (7.05 g, 16.61 mmol) and 2-tert-butyloxycarbonyl-2-hydroxyethylhydrazine (4.39 g, 24.91 mmol). The desired product was obtained as a yellow solid (3.82 g, 53%). 1H-NMR (DMSO-d6) δ 8.50 (s, 1H), 8.18 (m, 2H), 7.64 (m, 3H), 4.88 (m, 1H), 4.77 (t, 2H, J=6.1 Hz), 4.10 (t, 2H, J=5.5 Hz), 3.68 (m, 2H), 3.28 (m, 2H), 3.05 (m, 2H), 2.96 (m, 2H); LCMS RT=2.92 min; [M+H]+=438.1

Workup

  1. customThis compound was prepared in a similar fashion

Sources & evidence

ORD record
ord-b5c6a053c9ea4fbe9f1a185062e8dd54
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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