Formaldehyde → HCID 136090377, compound

HRID 131500Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:15][C:14]2[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=[C:9]([N:20]3[CH2:25][CH2:24][NH:23][C@@H:22]([CH2:26][CH2:27][O:28][CH3:29])[CH2:21]3)[C:8]=2[N:7]=1)=[O:5])[CH3:2].C=O.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([O:3][C:4]([C:6]1[S:15][C:14]2[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=[C:9]([N:20]3[CH2:25][CH2:24][N:23]([CH3:32])[C@@H:22]([CH2:26][CH2:27][O:28][CH3:29])[CH2:21]3)[C:8]=2[N:7]=1)=[O:5])[CH3:2]

Participants

Reactant 3

HCID 712Formaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 135457497HCID 135457497, compound

Product 1

HCID 136090377HCID 136090377, compoundYield 90.5%

Procedure

Using the method of Example 322, using (S)-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-4H-3-thia-1,4,9-triaza-benzo[f]azulene-2-carboxylic acid ethyl ester (300 mg, 0.72 mmol), formaldehyde (37%, w/w, aq) (72.9 mg, 0.90 mmol) and sodium triacetoxyborohydride (228.9 mg, 1.08 mmol) gives 280 mg (yield 90%) of (5)-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-4H-3-thia-1,4,9-triaza-benzo[f]azulene-2-carboxylic acid ethyl ester: mass spectrum (electrospray) (m/e): 430.0 (M+1), 428.1 (M−1); 1H NMR (400 MHz, DMSO-d6): 8.50 (s, 1H), 6.91-6.80 (m, 3H), 6.69-6.67 (m, 1H), 4.30 (q, 2H, J=6.8 Hz), 3.83-3.81 (m, 2H), 3.32-3.30 (m, 2H), 3.13 (s, 3H), 3.12-3.06 (m, 1H), 2.81-2.70 (m, 2H), 2.22-2.13 (m, 5H), 1.83-1.75 (m, 1H), 1.53-1.46 (m,1H), 1.27 (t, 3H, J=7.2 Hz). The dihydrochloride is form by adding 5 eq of acetyl chloride (256.2 mg, 3.26 mmol) to the free base (280 mg, 0.65 mmol) in ethanol. Collect the precipitates via vacuum filtration to afford 300 mg of yellow solid of the title compound: mass spectrum (electrospray) (m/e): C21H27N5O3S.2HCl, Calc. Mass (M+1): 430.1913,

Sources & evidence

ORD record: ord-c7ff56b6d224498593cc05db4fc30894
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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