Ammonium Chloride → HCID 18537301, compound

HRID 412984Notes

Reaction equation

HRID 412984 reaction equation
C(N1C2C=CC(N[C:17]3[CH:21]=[C:20]([S:22][CH3:23])[S:19][C:18]=3[C:24]([NH2:26])=[NH:25])=CC=2C2C1=CC=CC=2)C.[CH2:27]([N:29]1[C:41]2[CH:40]=[CH:39][C:38](NC3C=C(C(OC)=S)SC=3C)=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH3:28].C[Al](C)C.[Cl-].[NH4+:58]>C1(C)C=CC=CC=1>[CH2:27]([N:29]1[C:41]2[CH:40]=[CH:39][C:38]([NH:58][C:21]3[CH:17]=[C:18]([C:24]([NH2:26])=[NH:25])[S:19][C:20]=3[S:22][CH3:23])=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH3:28]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 86758695Methyl 4-[(9-ethylcarbazol-3-yl)amino]-5-methylthiothiophene-2-carboxylateHCID 136388348HCID 136388348, compound

Product 1

HCID 18537301HCID 18537301, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[((9-Ethylcarbazol-3-yl)amino]-5-methylthiothiophene-2-carboxamidine: The same procedure as in Example 253, step (b) was followed using 80 mg (0.21 mmol) of methyl 4-[(9-ethylcarbazol-3-yl)amino]-5-methylthiothiophene-2-carboxylate (as prepared in previous step), 2 mL of trimethylaluminum (2.0 M in toluene, 4 mmol), 216 mg of ammonium chloride (4 mmol) and 2 mL of toluene, and purified on a 2-g silica SPE column with 5% MeOH—CH2Cl2 to afford 56 mg (70%) of the title compound as a yellow foam. 1H-NMR (DMSO-d6, 400 MHz) δ 1.31 (t, 3H, J=7.0 Hz),2.50 (s, 3H), 4.42 (q, 2H, J=7.0Hz), 7.14 (m, 1H), 7.27 (dd, 1H, J=8.7,2.1 Hz), 7.43 (m, 1H), 7.56 (m, 2H), 7.82 (d, 1H, J=2.0 Hz), 7.87 (s, 1H), 7.92 (s, 1H), 8.10 (d, 1H, J=7.7 Hz), 9.11 (br s, 4H). Mass spectrum (ESI, m/z): Calcd. for C20H20N4S2, 381.1 (M+H), found 381.3.

Workup

  1. custompurified on a 2-g silica SPE column with 5% MeOH—CH2Cl2

Sources & evidence

ORD record
ord-bac6d7e1d62642e0b02d20d72995fb3a
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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