Acetic Acid → (S)-tert-butyl 4-(2-(3-((4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl) pyridin-2-yl)phenyl)carbamoyl)-N-methylbenzamido)ethyl)-1,4-diazepane-1-carboxylate

HRID 625463Notes

Reaction equation

HRID 625463 reaction equation
[CH2:1]([N:3]([CH2:45][CH3:46])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:24]=[CH:23][CH:22]=[C:14]([C:15]([N:17]([CH3:21])[CH2:18][CH:19]=O)=[O:16])[CH:13]=2)=[C:6]([C:26]2[CH:31]=[C:30]([C:32](=[O:44])[NH:33][C@@H:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:37][CH2:36][CH2:35]3)[CH:29]=[CH:28][N:27]=2)[CH:5]=1)[CH3:2].[N:47]1([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:53][CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.CC(O)=O.C([BH3-])#N.[Na+]>C(O)C.C(OCC)(=O)C>[CH2:45]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)[C:15]([N:17]([CH2:18][CH2:19][N:50]2[CH2:51][CH2:52][CH2:53][N:47]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:48][CH2:49]2)[CH3:21])=[O:16])=[O:25])=[C:6]([C:26]2[CH:31]=[C:30]([C:32](=[O:44])[NH:33][C@@H:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH2:37][CH2:36][CH2:35]3)[CH:29]=[CH:28][N:27]=2)[CH:5]=1)[CH3:46]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 86705976(S)-N-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-oxoethyl)isophthalamide

Product 1

HCID 68087739(S)-tert-butyl 4-(2-(3-((4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl) pyridin-2-yl)phenyl)carbamoyl)-N-methylbenzamido)ethyl)-1,4-diazepane-1-carboxylateYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (S)—N1-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-oxoethyl)isophthalamide (0.162 mmol, 100 mg) in ethanol (1 mL) were added tert-butyl 1,4-diazepane-1-carboxylate (0.324 mmol, 65 mg) and HOAc (0.324 mmol, 19.4 mg). The mixture was stirred at room temperature for 20 minutes, and then sodium cyanoborohydride (0.81 mmol, 51 mg) was added. The mixture was stirred for an additional 1 h, diluted with ethyl acetate, washed with sat. aqueous NaHCO3 and brine, dried, concentrated and purified by column to give a product (70 mg, 54%).

Workup

  1. stirringThe mixture was stirred for an additional 1 h
  2. washwashed with sat. aqueous NaHCO3 and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column

Sources & evidence

ORD record
ord-c2ab10e549474ada81b9b9775a63a7e3
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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