N-cyano-N'-phenylthiourea → HCID 178465973, compound

HRID 847181Notes

Reaction equation

HRID 847181 reaction equation
[C:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=S)#[N:2].C(N=C(NC1C=CC=CC=1)N[C@@H]1C2C=C(C#N)C=CC=2OC(C)(C)[C@H]1O)#N.[C:40]([C:43]1[CH:44]=[CH:45][C:46]2[O:51][C:50]([CH3:53])([CH3:52])[CH:49]([OH:54])[CH:48]([NH2:55])[C:47]=2[CH:56]=1)(=[O:42])[CH3:41].Cl.CN(C)CCCCCN=C=N>CN(C)C=O>[C:40]([C:43]1[CH:44]=[CH:45][C:46]2[O:51][C:50]([CH3:53])([CH3:52])[C@@H:49]([OH:54])[C@H:48]([NH:55][C:4]([NH:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:3][C:1]#[N:2])[C:47]=2[CH:56]=1)(=[O:42])[CH3:41]

Participants

6

Reactant 4

HCID 4711553N-cyano-N'-phenylthioureaHCID 156348051-(4-Amino-3-hydroxy-2,2-dimethylchroman-6-yl)ethan-1-oneHCID 574828161-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochlorideHCID 178431174HCID 178431174, compound

Product 1

HCID 178465973HCID 178465973, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of N-cyano-N'-phenylthiourea (0.98 g, 5.5 mmol, compound of Example 3, part A) and 6-acetyl-3,4-dihydro-2,2-dimethyl-3-hydroxy-4-amino-2H-1-benzopyran (1.0 g, 4.25 mmol, prepared according to Evans et al., J. Med. Chem., 1983, 26, 1582 and J. Med. Chem., 1986, 29, 2194) in dimethylformamide (6 ml) under argon was treated with 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (1.1 g, 5.5 mmol). The reaction was stirred at room temperature for 2 hours and then partitioned between 10% citric acid and ethyl acetate. The aqueous phase was reextracted with ethyl acetate and the combined extracts were washed with water, sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue was crystallized from ethyl acetate to yield the title compound (0.43 g), m.p. 182°-184° C.: 1H NMR (DMSO-d6) δ 9.45 (s, 1H), 7.82 (m, 3H), 7.44 (s, 3H), 7.25 (s, 1H), 6.96 (d, J=9.0 Hz, 1H), 6.0 (s, 1H), 5.1 (m, 1H), 4.15 (m, 1H), 3.8 (s, 1H), 2.61 (s, 3H), 1.52 (s, 3H), 1.29 (s, 3H); 13C NMR (CDCl3) δ 196.2, 159.3, 156.6, 137.6, 129.7, 129.1, 128.4, 124.7, 123.5, 123.3, 117.2, 116.6, 80.0, 71.2, 52.3, 26.7, 26.3, 18.6; IR (KBr) 3412.3, 2978.3, 2935.8, 2179.7, 1670.5, 1602.9, 1577.9, 1493.0, 1359.9, 1271.2, 1126.5 cm-1.

Workup

  1. custompartitioned between 10% citric acid and ethyl acetate
  2. washthe combined extracts were washed with water, sodium bicarbonate and brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d943fab05d9340b896c64cd4de716c1f
Source dataset
uspto-grants-1992_08
Patent number
US05140031

Reaction notes

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