Ethyl isocyanate → (+/-)-cis-3-Methyl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid ethylamide

HRID 561277Notes

Reaction equation

HRID 561277 reaction equation
[C:1]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20](Cl)(=[O:22])=[O:21])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][CH:25]1[CH2:30][CH2:29][N:28](CC2C=CC=CC=2)[CH2:27][CH:26]1[CH3:38].[C:39](OC(N1CCC(N)CC1)=O)(C)(C)C.[CH2:53]([N:55]=[C:56]=[O:57])[CH3:54].N(C(C)C)=C=O>>[CH2:53]([NH:55][C:56]([N:28]1[CH2:29][CH2:30][C@H:25]([NH:24][S:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[CH3:39])=[CH:11][CH:12]=2)(=[O:22])=[O:21])[C@H:26]([CH3:38])[CH2:27]1)=[O:57])[CH3:54]

Participants

6

Reactant 5

HCID 8022Ethyl isocyanateHCID 61277Isopropyl isocyanateHCID 12682914-Amino-1-Boc-piperidineHCID 161057574-Benzoylamino-naphthalene-1-sulfonyl chlorideHCID 222788353-Methyl-1-(phenylmethyl)-4-piperidinamine

Product 1

HCID 59656497(+/-)-cis-3-Methyl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid ethylamide

Procedure

The title compounds were made following general procedure in Scheme 5 and deprotection in scheme 4-1, substituting 4-(2-methyl-benzoylamino)-naphthalene-1-sulfonyl chloride for 4-benzoylamino-naphthalene-1-sulfonyl chloride, 4-amino-1-benzyl-3-methyl-piperidine for 4-amino-piperidine-1-carboxylic acid tert-butyl ester and ethyl isocyanate for 2-isocyanato-propane. 1H NMR (300 MHz, CDCl3) δ 8.71 (d, 1H), 8.40 (s, 1H), 8.28 (s, 2H), 7.98 (d, 1H), 7.68 (m, 3H), 7.41 (m, 1H), 7.30 (m, 2H), 5.21 (d, 1H), 4.36 (m, 1H), 3.35 (m, 2H), 3.15 (m, 4H), 2.98 (m, 2H), 2.57 (s, 3H), 1.71 (m, 2H), 1.40 (m, 2H), 1.10 (m, 1H), 1.03 (t, 3H) 0.63 (d, 3H); LC/MS m/z 509 (M+H)+.

Sources & evidence

ORD record
ord-c3350a0174604a27a0e9c5ca593d7d98
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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