Diisopropylethylamine → HCID 67155371, compound

HRID 389658Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][C:34]3=[O:39])[C:28]=2[O:40][CH:41]([F:43])[F:42])(=[O:26])=[O:25])[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20](O)=[O:21])[CH2:16][CH2:15]2)=[O:13])=[O:8])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=[N:79][C:78]2[N:81](O)N=N[C:77]=2C=1.ONC(=N)C>CN(C=O)C>[F:42][CH:41]([F:43])[O:40][C:28]1[C:29]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][C:34]2=[O:39])=[CH:30][CH:31]=[CH:32][C:27]=1[S:24]([NH:23][C@H:11]([C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[O:21][N:81]=[C:78]([CH3:77])[N:79]=2)[CH2:16][CH2:15]1)=[O:13])[CH2:10][NH:9][C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:8])(=[O:26])=[O:25]

Participants

Conditions

Temperature: 110 °C

Procedure

1-{(S)-3-[(5-Chloro-thiophene-2-carbonyl)-amino]-2-[2-difluoromethoxy-3-(2-oxo-piperidin-1-yl)-benzenesulfonylamino]-propionyl}-piperidine-4-carboxylic acid (69 mg, 0.104 mmol) from Example 10 in DMF (1 ml) and DIPEA (91 μl, 0.52 mmol) was treated with TBTU (35 mg, 0.109 mmol) and HOAT (3 mg, 0.021 mmol) and stirred for 2 min before N-hydroxy-acetamidine (9 mg, 0.115 mmol) was added. Stirring was continued for 1.25 h at RT. After that the reaction mixture was heated at 110° C. for 2 h. The mixture was purified by prep. HPLC. Yield after lyophilization: 44 mg, 60%, colorless, amorphous solid. MS (ES+): m/e=701.2/703.2, chloro pattern.

Workup

additionwas added
customThe mixture was purified by prep
customYield after lyophilization

Sources & evidence

ORD record: ord-1a3fcd11c7f04c10bcec936d3a950052
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378092B2

Reaction notes

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