Chloride → HCID 86758423, compound

HRID 2304287Notes

Reaction equation

HRID 2304287 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][CH:14]([NH:23][C:24](=[O:45])[CH2:25]NS(C3C(C)=C(C)C4OC(C)(C)CCC=4C=3C)(=O)=O)[C:15](=[O:22])[N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[NH2:46]C1C2C(=CC(CC(NC(=O)OC(C)(C)C)C(=O)N3CCCCC3)=CC=2)C=CN=1.NC(=O)C[C@H:78]([NH:82][S:83]([C:86]1[C:91]([CH3:92])=[CH:90][C:89]([O:93][CH3:94])=[C:88]([CH3:95])[C:87]=1[CH3:96])(=[O:85])=[O:84])[C:79](O)=[O:80].N[C@H](C(O)=O)CC(=O)N.[Cl-]>>[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][CH:14]([NH:23][C:24](=[O:45])[CH2:25][C@H:78]([NH:82][S:83]([C:86]3[C:91]([CH3:92])=[CH:90][C:89]([O:93][CH3:94])=[C:88]([CH3:95])[C:87]=3[CH3:96])(=[O:85])=[O:84])[C:79]([NH2:46])=[O:80])[C:15](=[O:22])[N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 5

HCID 312ChlorideHCID 6267(-)-AsparagineHCID 226656071,1-Dimethylethyl 1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl-carbamateHCID 22665631N-[1-[(1-Amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-yl)sulfonyl]amino]acetamide hydrochlorideHCID 57272383HCID 57272383, compound

Product 1

HCID 86758423HCID 86758423, compound

Procedure

The procedure described for 5c was used. Deprotection of 100 mg of 5a and coupling with 105 mg of (2S)-4-amino-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]-4-oxobutanoic acid (prepared from Asn-OH and 4-methoxy-2,3,6-trimethylsulfonylchloride (Mtr-chloride)using the procedure described for 5b) yielded the title compound (66 mg) as a mixture of diastereomers (1:1). 1H-NMR 400 MHz (CD3OD) δ: 1.20-1.68 (6H, m), 2.15 and 2.16 (3H, 2×s), 2.27-2.58 (2H, m), 2,57 (3H,s), 2.64 (3H, s), 2.93-3.57 (6H, m), 3.83 and 3.87 (3H, 2×s), 3.98-4.09 (1H, m), 5.07-5.19 (1H, m), 6.75 and 6.76 (1H, 2×s), 7.22-7.27 (1H, m), 7.55-7.79 (3H, m), 8.33-8.38 (1H, m).

Sources & evidence

ORD record
ord-ea81b81b3e7a4a6e847144ccdc5505b9
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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